Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

The Role of Oxazolidinones in l-Proline-Assisted Aldol-Type Reactions

Abstract

In this study, the formation of oxazolidinone intermediates along the reaction coordinates of two l-proline-catalyzed reactions was investigated using high-level quantum mechanical calculations. Our results suggest that the final product is produced via routes other than the currently-adopted catalytic cycle for l-proline, including routes where oxazolidinones are directly involved.

This is a preview of subscription content, log in to check access.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

References

  1. 1.

    Clayden J, Greeves N, Warren S, Wothers P (2000) Organic chemistry. Oxford University Press, Oxford

  2. 2.

    Tsuji H, Yagi F, Hattori H, Kita H (1994) J Catal 148:759

  3. 3.

    Climent MJ, Corma A, Iborra S, Velty A (2002) J Mol Catal A 327

  4. 4.

    Gijsen HJM, Wong C-H (1995) J Am Chem Soc 117:7585

  5. 5.

    Barbas CF III, Wang Y-F, Wong C-H (1990) J Am Chem Soc 112:2013

  6. 6.

    Zhong G, Hoffmann T, Lerner RA, Danieshefsky S, Barbas CF III (1997) J Am Chem Soc 119:8131

  7. 7.

    Cavill JL, Elliott RL, Evans G, Jones IL, Platts JA, Ruda AM, Tomkinson NCO (2006) Tetrahedron 62:410

  8. 8.

    Sakthivel K, Notz W, Bui T, Barbas CF III (2001) J Am Chem Soc 123:5260

  9. 9.

    Sunden H, Dahlin N, Ibrahem I, Adolfsson H, Cordova A (2005) Tetrahedron Lett 46:3385

  10. 10.

    Brown SP, Brochu MP, Sinz CJ, MacMillan DWC (2003) J Am Chem Soc 125:10808

  11. 11.

    Hayashi Y, Yamaguchi J, Hibino K, Shoji M (2003) Tetrahedron Lett 44:8293

  12. 12.

    Hayashi Y, Yamaguchi J, Sumiya T, Hibino K, Shoji M (2004) J Org Chem 69:5966

  13. 13.

    Iwamura H, Mathew SP, Blackmond DG (2004) J Am Chem Soc 126:11770

  14. 14.

    Iwamura H, Wells DH, Mathew SP, Klussmann M, Armstrong A, Blackmond DG (2004) J Am Chem Soc 126:16312

  15. 15.

    Mathew SP, Klussmann M, Wells A, Armstrong A, Blackmond DG (2006) Chem Comm 4291

  16. 16.

    Mathew SP, Iwamura H, Blackmond DG (2004) Angew Chem 43:3317

  17. 17.

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

  18. 18.

    Thomassigny C, Prim D, Greck C (2006) Tetrahedron Lett 47:1117

  19. 19.

    Hajos Z, Parrish DR (1974) J Org Chem 39:1615

  20. 20.

    Eder U, Sauer G, Wiechert R (1971) Angew Chem-Int Ed 10:496

  21. 21.

    Zotova N, Broadbelt LJ, Armstrong A, Blackmond DG (2009) Bioorg Med Chem Lett 19:3934

  22. 22.

    Zotova N, Franzke A, Armstrong A, Blackmond DG (2007) J Am Chem Soc 129:15100

  23. 23.

    Rankin KN, Gauld JW, Boyd RJ (2002) J Phys Chem A 106:5155

  24. 24.

    Poe S, Bogdan AR, Mason BP, Steinbacher JL, Opalka SM, McQuade DT (2008) J Org Chem 74:1574

  25. 25.

    Seebach D, Beck AK, Badine DM, Limbach M, Eschenmoser A, Treasurywala AM, Hobi R (2007) Helv Chim Acta 90:425

  26. 26.

    Gaussian 03, Revision E.01, Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery Jr JA, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian, Inc., Wallingford, CT

  27. 27.

    Becke AD (1993) J Chem Phys 98:5648

  28. 28.

    Lee C, Yang W, Parr R (1988) Phys Rev B 37:785

  29. 29.

    Hehre WJ, Ditchfield R, Pople JA (1972) J Chem Phys 56:2257

  30. 30.

    Hariharan PC, Pople JA (1973) Theor Chim Acta 28:213

  31. 31.

    Frisch MJ, Pople JA (1984) J Chem Phys 80:3265

  32. 32.

    Gonzales C, Schlegel B (1988) J Chem Phys 90:2154

  33. 33.

    Gonzales C, Schlegel B (1990) J Phys Chem 94:5523

  34. 34.

    McQuarrie D (2000) Statistical mechanics. University Science Books, Sausalito, CA

  35. 35.

    Scott A, Radom L (1996) J Phys Chem 100:16502

  36. 36.

    Zhao Y, Schultz NE, Truhlar DG (2006) J Chem Theo Comput 2:364

  37. 37.

    Fast PL, Sanchez ML, Truhlar DG (1999) Chem Phys Lett 306:407

  38. 38.

    Curtiss LA, Redfern PC, Raghavachari K, Rassolov V, Pople JA (1999) J Chem Phys 110:4703

  39. 39.

    Cossi M, Rega N, Scalmani G, Barone V (2002) J Comput Chem 24:669

  40. 40.

    Barone V, Cossi M, Tomasi J (1997) J Chem Phys 107:3210

  41. 41.

    Konstantinov IA, Broadbelt LJ (2009) Mol Sim (in press)

  42. 42.

    Yi-Fan H, Xin L (2008) Chin J Struct Chem 27:547

  43. 43.

    Isart C, Bures J, Vilarrasa J (2008) Tetrahedron Lett 49:5414

  44. 44.

    List B, Hoang L, Martin HJ (2004) Proc Natl Acad Sci 101:5839

  45. 45.

    Legault CY (2009) CYLview. Université de Sherbrooke, Canada

  46. 46.

    Zotova N, Moran A, Armstrong A, Blackmond DG (2009) Adv Synth Catal 351:2765

Download references

Acknowledgments

Funding through the Institute for Catalysis in Energy Processes (ICEP) at Northwestern University which is sponsored by DOE is acknowledged. Computational resources used for this study were available through NERSC. We also would like to acknowledge helpful discussions with Prof. Donna Blackmond at Imperial College, UK.

Author information

Correspondence to Linda J. Broadbelt.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Konstantinov, I.A., Broadbelt, L.J. The Role of Oxazolidinones in l-Proline-Assisted Aldol-Type Reactions. Top Catal 53, 1031–1038 (2010). https://doi.org/10.1007/s11244-010-9527-3

Download citation

Keywords

  • Oxazolidinones
  • l-proline
  • Aldol reactions
  • DFT