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Zirconium Lewis Acids

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Aldol Reactions

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Zirconium compounds were known to be used mostly for forming zirconium enolates by transmetallation for a subsequent aldol addition.1,2,3,4,5,6,7 Preformed lithium enolates were transmetallated to yield predominantly (Z)- or (E)-zirconium enolates. Irrespective of the geometry of the zirconium enolates used a preference to syn-configured aldol adducts is observed. This methodology was also deployed in highly diastereoselective aldol reactions to obtain chiral aldol adducts (Scheme 3.1.6.1).8,9,10,11,12,13,14

In addition to that, zirconium(IV) alkoxides are able to deprotonate α-carbon atoms of ketones.15,16 By subsequent reactions with aldehydes the corresponding aldol adducts were formed.17 The regioselectivity of this aldol addition is illustrated in Scheme 3.1.6.2.

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References

  1. Evans DA, McGee LR (1980) Tetrahedron Lett 21:3975

    Article  CAS  Google Scholar 

  2. Yamamoto Y, Maruyama K (1989) Tetrahedron Lett 30:4607

    Google Scholar 

  3. Brown DW, Campbell MM, Taylor AP, Zhang XA (1987) Tetrahedron Lett 28:985

    Article  CAS  Google Scholar 

  4. Panek JS, Bula OA (1988) Tetrahedron Lett 29:1661

    Article  CAS  Google Scholar 

  5. Curran DP, Chao JC (1990) Tetrahedron 46:7325

    Article  CAS  Google Scholar 

  6. Yamago S, Machii D, Nakamura E (1991) J Org Chem 56:2098

    Article  CAS  Google Scholar 

  7. Wipf P, Xu W, Smitrovich JH (1994) Tetrahedron 50:1935

    Article  CAS  Google Scholar 

  8. Evans DA, McGee LR (1981) J Am Chem Soc 103:2876

    Article  CAS  Google Scholar 

  9. d'Angelo J, Pecquet-Dumas F (1983) Tetrahedron Lett 24:1403

    Article  Google Scholar 

  10. Bernardi A, Colombo L, Gennari C, Prati L (1984) Tetrahedron 40:3769

    Article  CAS  Google Scholar 

  11. Katsuki T, Yamaguchi M (1985) Tetrahedron Lett 26:5807

    Article  CAS  Google Scholar 

  12. Sacha H, Waldmüller D, Braun M (1994) Chem Ber 127:1959

    Article  CAS  Google Scholar 

  13. Vicario JL, Badia D, Dominguez E, Rodriguez M, Carrillo L (2000) J Org Chem 65:3754

    Article  CAS  Google Scholar 

  14. Kurosu M, Lorca M (2001) J Org Chem 66:1205

    Article  CAS  Google Scholar 

  15. Stork G, Shiner CS, Winkler JD (1982) J Am Chem Soc 104:310

    Article  CAS  Google Scholar 

  16. Stork G, Winkler JD, Shiner CS (1982) J Am Chem Soc 104:3767

    Article  CAS  Google Scholar 

  17. Sasai H, Kirio Y, Shibasaki M (1990) J Org Chem 55:5306

    Article  CAS  Google Scholar 

  18. Hollis TK, Robinson NP, Bosnich B (1992) Tetrahedron Lett 33:6423

    Article  CAS  Google Scholar 

  19. Hollis TK, Odenkirk W, Robinson NP, Whelan J, Bosnich B (1993) Tetrahedron 49:5415

    Article  CAS  Google Scholar 

  20. Cozzi PG, Floriani C, Chiesi-Villa A, Rizzoli C (1994) Synlett 857

    Google Scholar 

  21. Cozzi PG, Floriani C (1995) J Chem Soc Perkin Trans 1:2557

    Article  Google Scholar 

  22. Kanno K-I, Takahashi T In: Acid Catalysis in Modern Organic Synthesis, Yamamoto H, Ishihara K (eds). Wiley, Weinheim, vol 2, p 828

    Google Scholar 

  23. Ishitani H, Yamashita Y, Shimizu H, Kobayashi S (2000) J Am Chem Soc 122:5403

    Article  CAS  Google Scholar 

  24. Yamashita Y, Ishitani H, Shimizu H, Kobayashi S (2002) J Am Chem Soc 124:3292

    Article  CAS  Google Scholar 

  25. Parmee ER, Hong Y, Tempkin O, Masamune S (1992) Tetrahedron Lett 33:1729

    Article  CAS  Google Scholar 

  26. Mikami K, Matsukawa S (1994) J Am Chem Soc 116:4077

    Article  CAS  Google Scholar 

  27. Mahrwald R (1995) Tetrahedron 51:9015

    Article  CAS  Google Scholar 

  28. Evans DA, MacMillan DWC, Campos KR (1997) J Am Chem Soc 119:10859

    Article  CAS  Google Scholar 

  29. Yanagisawa A, Matsumoto Y, Nakashima H, Asakawa K, Yamamoto H (1997) J Am Chem Soc 119:9319

    Article  CAS  Google Scholar 

  30. Denmark SE, Wong KT, Stavenger RA (1997) J Am Chem Soc 119:2333

    Article  CAS  Google Scholar 

  31. Northrup AB, MacMillan DWC (2002) J Am Chem Soc 124:6798

    Article  CAS  Google Scholar 

  32. Yanagisawa A, Matsumoto Y, Asakawa K, Yamamoto H (2002) Tetrahedron 58:8331

    Article  CAS  Google Scholar 

  33. Denmark SE, Wynn T, Beutner GL (2002) J Am Chem Soc 124:13405

    Article  CAS  Google Scholar 

  34. Wadamoto M, Ozawa N, Yanagisawa A, Yamamoto H (2003) J Org Chem 68:5593

    Article  CAS  Google Scholar 

  35. Evans DA, Johnson DS (1999) Org Lett 1:595

    Article  CAS  Google Scholar 

  36. Nakamura M, Hamashima Y, Usuda H, Kanai M, Shibasaki M (2000) Angew Chem Int Ed 39:1650

    Article  Google Scholar 

  37. Evans DA, Scheidt KA, Johnston JN, Willis MC (2001) J Am Chem Soc 123:4480

    Article  CAS  Google Scholar 

  38. Posner GH, Dai H, Bull DS, Lee JK, Eydoux F, Ishihara Y, Welsh W, Pryor N, Petr JrS (1996) J Org Chem 61:671

    Article  CAS  Google Scholar 

  39. Terada M, Matsumoto Y, Nakamura Y, Mikami K (1997) Chem Commun 281

    Google Scholar 

  40. Terada M, Matsumoto Y, Nakamura Y, Mikami K (1999) Inorg Chim Acta 296:267

    Article  CAS  Google Scholar 

  41. Ribe S, Wipf P (2001) Chem Commun 299

    Google Scholar 

  42. Kobayashi S, Saito S, Ueno M, Yamashita Y (2003) Chem Commun 2016

    Google Scholar 

  43. Sauvé G, Shwartz DA, Ruest L, Deslongchamps P (1984) Can J Chem 62:2929

    Article  Google Scholar 

  44. Bernet B, Bishop PM, Caron M, Kawamata T, Roy BL, Ruest L, Sauvé G, Soucy P, Deslongchamps P (1985) Can J Chem 63:2810

    Article  CAS  Google Scholar 

  45. Corey EJ, Reichardt GA, Kania R (1993) Tetrahedron Lett 44:6977

    Article  Google Scholar 

  46. Kobayashi J, Nakamura M, Mori Y, Yamashita Y, Kobayashi S (2004) J Am Chem Soc 126:9192

    Article  CAS  Google Scholar 

  47. Isoda T, Akiyama R, Oyamada H, Kobayashi S (2006) Adv Synth Catal 348:1813

    Article  CAS  Google Scholar 

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Editors and Affiliations

  1. Institute of Chemistry, Humboldt University, Brook Taylor Str. 2, Berlin, 12 489, Germany

    Rainer Mahrwald

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(2009). Zirconium Lewis Acids. In: Mahrwald, R. (eds) Aldol Reactions. Springer, Dordrecht. https://doi.org/10.1007/978-1-4020-8701-1_13

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