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Carbene Catalysis: Beyond the Benzoin and Stetter Reactions

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Inventing Reactions

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 44))

Abstract

The discovery and development of new N-heterocyclic carbene-catalyzed reaction is described. Based on inspiration from nature, we have taken thiazolium-based approaches to umpolung reactivity and invented a suite of related reactions involving acyl anions, homoenolate, and enolate nucleophiles all generated under catalytic conditions.

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Abbreviations

Ar:

Aryl

Bn:

Benzyl

Cy:

Cyclohexyl

DABCO:

1,4-Diazabicyclo[2,2,2]octane

DBU:

1,8-Diazabicyclo[5.4.0]undec-7-ene

DCM:

Dichloromethane

DMAP:

N,N-4-dimethylaminopyridine

E+ :

Electrophile

Ee:

Enantiomeric excess

Et:

Ethyl

H:

Hour

HOMO:

Highest occupied molecular orbital

i-Pr:

iso-Propyl

L.A.:

Lewis acid

Me:

Methyl

Mes:

Mesityl

NHC:

N-heterocyclic carbene

NMR:

Nuclear magnetic resonance

Np:

Naphthyl

Nu− :

Nucleophile

p :

Para

Ph:

Phenyl

Pr:

Propyl

TADDOL:

2,2-Dimethyl-α,α,α′,α′-tetraphenyl-1,3-dioxolane-4,5-dimethanol

TBD:

1,5,7-Triazabicyclo[4.4.0]dec-5-ene

TBDPS:

tert-Butyldiphenylsilyl

t-Bu:

tert-Butyl

Tf:

Trifluoromethanesulfonyl

THF:

Tetrahydrofuran

Tol:

Tolyl

Ts:

p-Toluenesulfonyl

X− :

Counterion

References

  1. Ojima I (ed) (2010) Catalytic asymmetric synthesis. Wiley-VCH, Weinheim

    Google Scholar 

  2. Eder U, Sauer G, Wiechert R (1971) Angew Chem 83:492–493; Angew Chem Int Ed 10:496–497

    Google Scholar 

  3. Berkessel A, Gröger H (eds) (2005) Asymmetric organocatalysis. Wiley-VCH, Weinheim

    Google Scholar 

  4. List B (2007) Chem Rev 107:5413

    Article  CAS  Google Scholar 

  5. Enders D, Grondal C, Hüttl MRM (2007) Angew Chem 119:1590; Angew Chem Int Ed 46:1570

    Google Scholar 

  6. Almasi D, Alonso DA, Nájera C (2007) Tetrahedron: Asymmetry 18:299

    Article  CAS  Google Scholar 

  7. Erkkilä A, Majander I, Pihko PM (2007) Chem Rev 107:5416

    Article  CAS  Google Scholar 

  8. Dondoni A, Massi A (2008) Angew Chem Int Ed 47:4638

    Article  CAS  Google Scholar 

  9. Grondal C, Jeanty M, Enders D (2010) Nat Chem 2:167

    Article  CAS  Google Scholar 

  10. Doyle AG, Jacobsen EN (2007) Chem Rev 107:5713

    Article  CAS  Google Scholar 

  11. Taylor MS, Jacobsen EN (2006) Angew Chem Int Ed 45:1520

    Article  CAS  Google Scholar 

  12. Yu X, Wang W (2008) Chem Asian J 3:516

    Article  CAS  Google Scholar 

  13. Zhang ZG, Schreiner PR (2009) Chem Soc Rev 38:1187

    Article  CAS  Google Scholar 

  14. Terada M (2010) Synthesis 1929

    Google Scholar 

  15. Biddle MM, Lin M, Scheidt KA (2007) J Am Chem Soc 129:3830

    Article  CAS  Google Scholar 

  16. Palomo C, Oiarbide M, Lopez R (2009) Chem Soc Rev 38:632

    Article  CAS  Google Scholar 

  17. Ooi T, Maruoka K (2007) Angew Chem Int Ed 46:4222

    Article  CAS  Google Scholar 

  18. List B (2001) Synlett 1675

    Google Scholar 

  19. List B (2004) Acc Chem Res 37:548

    Article  CAS  Google Scholar 

  20. Mukherjee S, Yang JW, Hoffmann S, List B (2007) Chem Rev 107:5471

    Article  CAS  Google Scholar 

  21. Melchiorre P, Marigo M, Carlone A, Bartoli G (2008) Angew Chem Int Ed 47:6138

    Article  CAS  Google Scholar 

  22. Denmark SE, Beutner GL (2008) Angew Chem Int Ed 47:1560

    Article  CAS  Google Scholar 

  23. Fu GC (2004) Acc Chem Res 37:542

    Article  CAS  Google Scholar 

  24. Miller SJ (2004) Acc Chem Res 37:601

    Article  CAS  Google Scholar 

  25. Enders D, Narine AA (2008) J Org Chem 73:7857

    Article  CAS  Google Scholar 

  26. Williams RR (1936) J Am Chem Soc 58:1063

    Article  CAS  Google Scholar 

  27. Mizuhara S, Handler P (1954) J Am Chem Soc 76:571

    Article  CAS  Google Scholar 

  28. Enders D, Balensiefer T (2004) Acc Chem Res 37:534

    Article  CAS  Google Scholar 

  29. Nair V, Bindu S, Sreekumar V (2004) Angew Chem 116:5240; Angew Chem Int Ed 43:5130

    Google Scholar 

  30. Zeitler K (2005) Angew Chem 117:7674; Angew Chem Int Ed 44:7506

    Google Scholar 

  31. Marion N, Diez-Gonzalez S, Nolan SP (2007) Angew Chem 119:3046; Angew Chem Int Ed 46:2988

    Google Scholar 

  32. Enders D, Niemeier O, Henseler A (2007) Chem Rev 107:5606

    Article  CAS  Google Scholar 

  33. Zeitler K (2008) In: Reetz MT, List B, Jaroch S, Weinmann H (eds) Organocatalysis. Springer, Heidelberg, pp 183–206

    Google Scholar 

  34. Glorius F, Hirano K (2008) In: Reetz MT, List B, Jaroch S, Weinmann H (eds) Organocatalysis. Springer, Heidelberg, pp 159–181

    Google Scholar 

  35. Biju AT, Kuhl N, Glorius (2011) Acc Chem Res 44 (Article ASAP)

    Google Scholar 

  36. Wanzlick H-W (1962) Angew Chem Int Ed Engl 1:75

    Article  Google Scholar 

  37. Wanzlick H-W, Kleiner H-J (1964) Angew Chem Int Ed Engl 3:65

    Article  Google Scholar 

  38. Schönherr H-J, Wanzlick H-W (1970) Chem Ber 103:1037

    Article  Google Scholar 

  39. Schönherr H-J, Wanzlick H-W (1970) Justus Liebigs Ann Chem 731:176

    Article  Google Scholar 

  40. Walentow R, Wanzlick HWZ (1970) Naturforsch B: Chem Sci 25:1421

    Google Scholar 

  41. Marion N, Diez-Gonzalez S, Nolan SP (2007) Angew Chem 119:3046; Angew Chem Int Ed 46:2988

    Google Scholar 

  42. Arduengo AJ III (1999) Acc Chem Res 32:913

    Article  CAS  Google Scholar 

  43. Seebach D (1969) Synthesis 1:17

    Article  CAS  Google Scholar 

  44. Gröbel BT, Seebach D (1977) Synthesis 357

    Google Scholar 

  45. Page PCB, Van Niel MB, Prodger JC (1989) Tetrahedron 45:7643

    Article  CAS  Google Scholar 

  46. Yus M, Najera C, Foubelo F (2003) Tetrahedron 59:6147

    Article  CAS  Google Scholar 

  47. Corey EJ, Seebach D (1965) Angew Chem Int Ed Engl 4:1075

    Article  CAS  Google Scholar 

  48. Seebach D, Corey EJ (1965) Angew Chem Int Ed Engl 4:1077

    Article  Google Scholar 

  49. Wöhler F, Liebig J (1832) Ann Pharm 3:249

    Article  Google Scholar 

  50. Lapworth A (1903) Transactions 83:995

    CAS  Google Scholar 

  51. Ugai T, Tanaka S, Dokawa S (1943) J Pharm Soc Jpn (Yakugaku Zasshi) 63:296

    Google Scholar 

  52. Breslow R (1958) J Am Chem Soc 80:3719

    Article  CAS  Google Scholar 

  53. Breslow R, Schmuck C (1996) Tetrahedron Lett 37:8241

    Article  CAS  Google Scholar 

  54. White MJ, Leeper FJ (2001) J Org Chem 66:5124

    Article  CAS  Google Scholar 

  55. Phillips EM, Chan A, Scheidt KA (2009) Aldrichim Acta 42:55

    CAS  Google Scholar 

  56. Sheehan JC, Hunneman DH (1966) J Am Chem Soc 88:3666

    Article  CAS  Google Scholar 

  57. Bredig G, Fiske PS (1912) Biochem Z 46:7

    Google Scholar 

  58. Bredig G, Minaeff M (1932) Biochem Z 249:241

    CAS  Google Scholar 

  59. Prelog V, Wilhelm M (1954) Helv Chim Acta 37:1634

    Article  CAS  Google Scholar 

  60. Enders D, Kallfass U (2002) Angew Chem Int Ed 41:1743

    Article  CAS  Google Scholar 

  61. Stetter H (1976) Angew Chem Int Ed Engl 15:639

    Article  Google Scholar 

  62. Harrington PE, Tius MA (1999) Org Lett 1:649

    Article  CAS  Google Scholar 

  63. Anjaiah S, Chandrasekhar S, Gree R (2004) Adv Syn Cat 346:1329

    Article  CAS  Google Scholar 

  64. Enders D, Balensiefer T (2004) Acc Chem Res 37:534

    Article  CAS  Google Scholar 

  65. Kerr MS, de Alaniz JR, Rovis T (2002) J Am Chem Soc 124:10298

    Article  CAS  Google Scholar 

  66. Kerr MS, Rovis T (2004) J Am Chem Soc 126:8876

    Article  CAS  Google Scholar 

  67. de Alaniz JR, Rovis T (2005) J Am Chem Soc 127:6284

    Article  CAS  Google Scholar 

  68. Moore J, Silvestri AP, de Alaniz JR, DiRocco DA, Rovis T (2011) Org Lett 13:1742

    Article  CAS  Google Scholar 

  69. Liu Q, Rovis T (2009) Org Lett 11:2856

    Article  CAS  Google Scholar 

  70. DiRocco DA, Oberg KM, Dalton DM, Rovis T (2009) J Am Chem Soc 131:10872

    Article  CAS  Google Scholar 

  71. DiRocco DA, Rovis T (2011) J Am Chem Soc 133:10402

    Article  CAS  Google Scholar 

  72. Um JM, DiRocco DA, Noey EL, Rovis T, Houk KN (2011) J Am Chem Soc 133:11249

    Article  CAS  Google Scholar 

  73. Jousseaume T, Wurz NE, Glorius F (2011) Angew Chem Int Ed 50:1410

    Article  CAS  Google Scholar 

  74. Page PCB, Klair SS, Rosenthal S (1990) Chem Soc Rev 19:147

    Article  CAS  Google Scholar 

  75. Cirillo PF, Panek JS (1992) Org Prep Proced Int 24:553

    Article  CAS  Google Scholar 

  76. Bonini BF, Comes-Franchini M, Fochi M, Mazzanti G, Ricci A (1998) J Organomet Chem 567:181

    Article  CAS  Google Scholar 

  77. Brook AG (1974) Acc Chem Res 7:77

    Article  CAS  Google Scholar 

  78. Schinzer D, Heathcock CH (1981) Tetrahedron Lett 22:1881

    Article  CAS  Google Scholar 

  79. Ricci A, Degl’Innocenti A, Mordini A, Reginato G, Colotta V (1987) Gazz Chim Ital 117:645

    Google Scholar 

  80. Mattson AE, Bharadwaj AR, Scheidt KA (2004) J Am Chem Soc 126:2314

    Article  CAS  Google Scholar 

  81. Xin LH, Johnson JS (2003) Angew Chem Int Ed 42:2534

    Article  CAS  Google Scholar 

  82. Bharadwaj AR, Scheidt KA (2004) Org Lett 6:2465

    Article  CAS  Google Scholar 

  83. Mattson AE, Bharadwaj AR, Zuhl AM, Scheidt KA (2006) J Org Chem 71:5715

    Article  CAS  Google Scholar 

  84. Mattson AE, Scheidt KA (2004) Org Lett 6:4363

    Article  CAS  Google Scholar 

  85. Stetter H, Lorenz G (1985) Chem Ber 118:1115

    Article  CAS  Google Scholar 

  86. Hayakawa S, Michiue T, Okamoto M, Hatakeyama S, Ohta S (1988) Heterocycles 27:457

    Article  CAS  Google Scholar 

  87. Evans DA, Fandrick KR, Song H-J (2005) J Am Chem Soc 127:8942

    Article  CAS  Google Scholar 

  88. Myers MC, Bharadwaj AR, Milgram BC, Scheidt KA (2005) J Am Chem Soc 127:14675

    Article  CAS  Google Scholar 

  89. Davies DH, Hall J, Smith EH (1991) J Chem Soc Perkins Trans 1:2691

    Google Scholar 

  90. Ji J-X, Chan ASC (2010) In: Ojima I (ed) Catalytic asymmetric synthesis, 3rd edn. Wiley-VCH, Weinheim, pp 439–498

    Google Scholar 

  91. Csákÿ AG, de la Herrán GD, Murcia MC (2010) Chem Soc Rev 39:4080

    Article  CAS  Google Scholar 

  92. Nickhorn A, Lambert JL (1964) J Am Chem Soc 86:4604

    Google Scholar 

  93. Freeman JP, Plonka JH (1966) J Am Chem Soc 88:3662

    Article  CAS  Google Scholar 

  94. Nair V, Vellalath S, Babu BP (2008) Chem Soc Rev 37:2691

    Article  CAS  Google Scholar 

  95. Natural Products Gordon Research Conference, Tilton

    Google Scholar 

  96. Chan A, Scheidt KA (2005) Org Lett 7:905

    Article  CAS  Google Scholar 

  97. Burstein C, Glorius F (2004) Angew Chem Int Ed 43:6205

    Article  CAS  Google Scholar 

  98. Sohn SS, Rosen EL, Bode JW (2004) J Am Chem Soc 126:14370

    Article  CAS  Google Scholar 

  99. Chan A, Scheidt KA (2006) J Am Chem Soc 128:4558

    Article  CAS  Google Scholar 

  100. Maki BE, Chan A, Phillips EM, Scheidt KA (2007) Org Lett 9:371

    Article  CAS  Google Scholar 

  101. Maki BE, Scheidt KA (2008) Org Lett 10:4331

    Article  CAS  Google Scholar 

  102. Maki BE, Chan A, Phillips EM, Scheidt KA (2009) Tetrahedron 65:3102

    Article  CAS  Google Scholar 

  103. De Sarkar S, Studer A (2010) Angew Chem Int Ed 49:9266

    Article  CAS  Google Scholar 

  104. De Sarkar S, Studer A (2010) Org Lett 12:1992

    Article  CAS  Google Scholar 

  105. De Sarkar S, Grimme S, Studer A (2010) J Am Chem Soc 132:1190

    Article  CAS  Google Scholar 

  106. De Sarkar S, Biswas A, Song CH, Studer A (2011) Synthesis 1974

    Google Scholar 

  107. Padwa A (ed) (1984) 1,3-Dipolar cycloaddition chemistry. Wiley, New York

    Google Scholar 

  108. Gothelf KV, Jørgensen KA (1998) Chem Rev 98:863

    Article  CAS  Google Scholar 

  109. Pearson WH (2002) Pure Appl Chem 74:1339

    Article  CAS  Google Scholar 

  110. Carruthers W (1990) Cycloaddition reactions in organic synthesis. Pergamon, Elmsford

    Google Scholar 

  111. Dorn H, Otto A (1968) Chem Ber 101:3287

    Article  CAS  Google Scholar 

  112. Shintani R, Fu GC (2003) J Am Chem Soc 125:10778

    Article  CAS  Google Scholar 

  113. Suárez A, Downey CW, Fu GC (2005) J Am Chem Soc 127:11244

    Article  CAS  Google Scholar 

  114. Shintani R, Hayashi T (2006) J Am Chem Soc 128:6330

    Article  CAS  Google Scholar 

  115. Suga H, Funyu A, Kakehi A (2007) Org Lett 9:97

    Article  CAS  Google Scholar 

  116. Syroeshkina YS, Petukhova VY, Kachala VV, Nelyubina YV, Makhova NN (2010) Russ Chem Bull Int Ed 59:1433

    Article  CAS  Google Scholar 

  117. Chan A, Scheidt KA (2007) J Am Chem Soc 129:5334

    Article  CAS  Google Scholar 

  118. He M, Bode JW (2005) Org Lett 7:3131–3134

    Article  CAS  Google Scholar 

  119. Confalone PN, Huie EM (1988) Org React (NY) 36:1

    CAS  Google Scholar 

  120. Gothelf KV, Jørgensen KA (2000) Chem Commun 1449

    Google Scholar 

  121. Jen WS, Wiener JJM, MacMillan DWC (2000) J Am Chem Soc 122:9874

    Article  CAS  Google Scholar 

  122. Martin JN, Jones RCF (2002) Synthetic applications of 1,3-dipolar cycloaddition chemistry toward heterocycles and natural products. In: Padwa A, Pearson WH (eds) The chemistry of heterocyclic compounds series, vol. 59. Wiley, Chichester pp 1–81

    Google Scholar 

  123. Feuer H, Torssell K (2008) Nitrile oxides, nitrones, and nitronates in organic synthesis: novel strategies in synthesis, 2nd edn. Wiley-Interscience, Hoboken

    Google Scholar 

  124. Phillips EM, Reynolds TE, Scheidt KA (2008) J Am Chem Soc 130:2416

    Article  CAS  Google Scholar 

  125. Bryans JS, Wustrow DJ (1999) Med Res Rev 19:149

    Article  CAS  Google Scholar 

  126. Tassone DM, Boyce E, Guyer J, Nuzum D (2007) Clin Ther 29:26

    Article  CAS  Google Scholar 

  127. Cooper JR, Bloom FE, Roth RH (2003) The biochemical basis of neuropharmacology, 8th edn. Oxford University Press, Oxford

    Google Scholar 

  128. Sibi MP, Shay JJ, Liu M, Jasperse CP (1998) J Am Chem Soc 120:6615

    Article  CAS  Google Scholar 

  129. Myers JK, Jacobsen EN (1999) J Am Chem Soc 121:8959

    Article  CAS  Google Scholar 

  130. Horstmann TE, Guerin DJ, Miller SJ (2000) Angew Chem Int Ed 39:3635

    Article  Google Scholar 

  131. Doi H, Sakai T, Iguchi M, Yamada K, Tomioka K (2003) J Am Chem Soc 125:2886

    Article  CAS  Google Scholar 

  132. Chan A, Scheidt KA (2006) J Am Chem Soc 128:4558

    Article  CAS  Google Scholar 

  133. He M, Struble JR, Bode JW (2006) J Am Chem Soc 128:8418–8420

    Article  CAS  Google Scholar 

  134. He M, Uc GJ, Bode JW (2006) J Am Chem Soc 128:15088–15089

    Article  CAS  Google Scholar 

  135. Phillips EM, Wadamoto M, Chan A, Scheidt KA (2007) Angew Chem Int Ed 46:3107

    Google Scholar 

  136. Wadamoto M, Phillips EM, Reynolds TE, Scheidt KA (2007) J Am Chem Soc 129:10098

    Article  CAS  Google Scholar 

  137. Phillips EM, Wadamoto M, Scheidt KA (2009) Synthesis 687

    Google Scholar 

  138. Phillips EM, Roberts JM, Scheidt KA (2010) Org Lett 12:2830

    Article  CAS  Google Scholar 

  139. Dias LC, Aguilar AM (2008) Chem Soc Rev 37:451

    Google Scholar 

  140. Kimball DB, Silks LA III (2006) Curr Org Chem 10:1975

    Article  CAS  Google Scholar 

  141. Phillips EM, Wadamoto M, Roth HS, Ott AW, Scheidt KA (2009) Org Lett 11:105

    Article  CAS  Google Scholar 

  142. Kawanaka Y, Phillips EM, Scheidt KA (2009) J Am Chem Soc 131:18028

    Article  CAS  Google Scholar 

  143. He M, Bode JW (2005) Org Lett 7:3131

    Article  CAS  Google Scholar 

  144. Raup DEA, Cardinal-David B, Holte D (2010) Nat Chem 2:766

    Article  CAS  Google Scholar 

  145. Sugiura M, Kobayashi S (2005) Angew Chem Int Ed 44:5176

    Article  CAS  Google Scholar 

  146. Lee SK, Tambar UK, Perl NR, Leighton JL (2010) Tetrahedron 66:4769

    Article  CAS  Google Scholar 

  147. Feske MI, Buitrago Santanilla A, Leighton JL (2010) Org Lett 12:688

    Article  CAS  Google Scholar 

  148. Burgess K, Perry MC (2003) Tetrahedron: Asymmetry 14:951

    Article  CAS  Google Scholar 

  149. Nolan SP (ed) (2006) N-heterocyclic carbenes in synthesis. Wiley-VCH, Weinheim

    Google Scholar 

  150. Glorius F (2007) Top Organomet Chem 21:1

    Article  CAS  Google Scholar 

  151. Hahn FE, Jahnke MC (2008) Angew Chem Int Ed 47:3122

    Article  CAS  Google Scholar 

  152. Nair V, Vellalath S, Poonoth S, Suresh E (2006) J Am Chem Soc 128:8736

    Article  CAS  Google Scholar 

  153. Chiang P-C, Kaeobamrung J, Bode JW (2007) J Am Chem Soc 129:3520

    Article  CAS  Google Scholar 

  154. Cardinal-David B, Raup DEA, Scheidt KA (2010) J Am Chem Soc 132:5345

    Article  CAS  Google Scholar 

  155. Patel D, Liddle ST, Mungur SA, Rodden M, Blake AJ, Arnold PL (2006) J Chem Soc Chem Commun 1124

    Google Scholar 

  156. Evans DA, Johnson JS, Olhava EJ (2000) J Am Chem Soc 122:1635

    Article  CAS  Google Scholar 

  157. Wada E, Koga H, Kumaran G (2002) Tetrahedron Lett 43:9397

    Article  CAS  Google Scholar 

  158. Koga H, Wada E (2003) Tetrahedron Lett 44:715

    Article  CAS  Google Scholar 

  159. Kurosu M, Porter JR, Foley MA (2004) Tetrahedron Lett 45:145

    Article  CAS  Google Scholar 

  160. Ünaleroglu C, Temelli B, Demir AS (2004) Synthesis 2574

    Google Scholar 

  161. Hughes KD, Nguyen T-LN, Dyckman D, Dulay D, Boyko WJ, Giuliano RM (2005) Tetrahedron: Asymmetry 16:273

    Article  CAS  Google Scholar 

  162. Evans DA, Dunn TB, Kvoernø L, Beauchemin A, Raymer B, Olhava EJ, Mulder JA, Juhl M, Kagechika K, Favor DA (2007) Angew Chem 119:4782; Angew Chem Int Ed 46:4698

    Google Scholar 

  163. Kaeobamrung J, Bode JW (2009) Org Lett 11:677–680

    Article  CAS  Google Scholar 

  164. Cohen DT, Cardinal-David B, Scheidt KA (2011) Angew Chem Int Ed 50:1678

    Google Scholar 

  165. Li Y, Zhao Z-A, He H, You S-L (2008) Adv Synth Catal 350:1885

    Article  CAS  Google Scholar 

  166. Matsuoka Y, Ishida Y, Saigo K (2008) Tetrahedron Lett 49:2985

    Article  CAS  Google Scholar 

  167. Seebach D, Beck AK, Heckel A (2001) Angew Chem Int Ed 40:92

    Article  CAS  Google Scholar 

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Acknowledgments

We gratefully acknowledge Northwestern University, the National Institute of General Medical Sciences (R01GM73072), the Sloan Foundation, Abbott Laboratories, Amgen, AstraZeneca, Boehringer-Ingelheim, GlaxoSmithKline, and Novartis for their generous support of our research program. FQRNT (Fonds québécois de la recherche sur la nature et les technologies) is also gratefully acknowledged for a postdoctoral fellowship to B.C.D. Lastly, we thank all current and former Scheidt group members for their heartfelt dedication and lasting contributions.

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  1. Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Northwestern University, Evanston, IL, 60208, USA

    Benoit Cardinal-David & Karl A. Scheidt

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  1. Benoit Cardinal-David
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  2. Karl A. Scheidt
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Correspondence to Karl A. Scheidt .

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  1. , FB Chemie - Organische Chemie, TU Kaiserslautern, Erwin-Schrödinger-Str. 54, Kaiserslautern, 67663, Germany

    Lukas J. Gooßen

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Cardinal-David, B., Scheidt, K.A. (2012). Carbene Catalysis: Beyond the Benzoin and Stetter Reactions. In: Gooßen, L. (eds) Inventing Reactions. Topics in Organometallic Chemistry, vol 44. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3418_2012_47

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