Alkynes to (E)-enolates using tandem catalysis: Stereoselective anti-aldol and syn-[3,3]-rearrangement reactions

Tetrahedron

Volumn 66, Issue 33, 2010, Pages 6429-6436

  Grimster, Neil P ^a   Wilton, Donna A A ^a   Chan, Louis K M ^a   Godfrey, Christopher R A ^b   Green, Clive ^c   Owen, Dafydd R ^d   Gaunt, Matthew J ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b SYNGENTA CROP PROTECTION AG   (Switzerland)

^c ASTRAZENECA   (United Kingdom)

^d PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

Alkyne; Enolate; Stereoselective aldol; Stereoselective Sigmatropic rearrangement; Tandem catalysis

Indexed keywords

3 TERT BUTYL 2 (43 HYDROXY 4 METHYL 2 PHENYL PENTANOYL)CYCLOPENTANONE; 4 (TERT BUTYL) 3 (2 (1 PHENYLALLYL)OCTANOYL) OXAZOLIDIN 2 ONE; 4 TERT BUTYL 3 (2,3 DIPHENYLPENT 4 ENOYL) OXAZOLIDIN 2 ONE; 4 TERT BUTYL 3 (3 CYCLOHEXYL 3 HYDROXY 2 PHENYL PENTANOYL)OXAZOLIDIN 2 ONE; 4 TERT BUTYL 3 (3 HYDROXY 2 PHENYLHEXANOYL)OXAZOLIDIN 2 ONE; 4 TERT BUTYL 3 (4 METHYL 2 PHENYL 3 (TRIPHENYLSILYLOXY)PENTANOYL)OXAZOLIDIN 2 ONE; 4,4 DIMETHYL 3 [2 PHENYL 3 (4 TRILFUOROMETHYL PHENYL) HEX 4 ENOYL] OXAZOLIDIN 2 ONE; 4,4 DIMETHYL 3 [2 PHENYL 3 (4 TRILFUOROMETHYL PHENYL) PEN 4 ENOYL] OXAZOLIDIN 2 ONE; ALKYNE; BRONSTED ACID; CARBONYL DERIVATIVE; ENOLATE; LEWIS ACID; RAC 3 (2 ((2,6 DIMETHOXYPHENYL)(TRIPHENYLSILYLOXY)METHYL)OCTANOYL) 4,4 DIMETHYLOXAZOLIDIN 2 ONE; RAC 3 (2 CYCLOHEXYL 3 PHENYL PENT 4 ENOYL) 4,4 DIEMTHYLOXAZOLIDIN 2 ONE; RAC 3 (2,3 DIPHENYL 3 (TRIISOPROPYLSILYLOXY)PROANOYL) 4,4 DIMETHYLOXAZOLIDIN 2 ONE; RAC 3 (2,3 DIPHENYL 3 (TRIPHENYLSILYLOXY)PROANOYL) 4,4 DIMETHYLOXAZOLIDIN 2 ONE; RAC 3 (2,3 DIPHENYL PEN 4 ENOYL) 4,4 DIMETHYLOXY AZOLIDIN 2 ONE; RAC 3 (2,4 DIPHENYL 3 (TRIPHENYLSILYLOXY)PENTANOYL) 4,4 DIMETHYLOXAZOLIDIN 2 ONE; RAC 3 (3 CYCLOHEXYL 2 PHENYL 3 (TRIPHENYLSILYLOXY)PROPANOYL) 4,4 DIMETHYLOXAZOLIDIN 2 ONE; RAC 4,4 DIMETHYL 3 (2 (PHENYL (TRIPHENYLSILYLOXY)METHYL)OCTANOYL) OXAZOLIDIN 2 ONE; RAC 4,4 DIMETHYL 3 (2 METHYL 3 PHENYL 3 (TRIPHENYLSILYLOXY)PROANOYL) OXAZOLIDIN 2 ONE; RAC 4,4 DIMETHYL 3 (2 PHENYL 3 (TRIPHENYLSILYLOXY)HEXANOYL) OXAZOLIDIN 2 ONE; RAC 4,4 DIMETHYL 3 (2 PHENYL 3 ETHYL PENT 4 ENOYL) OXAZOLIDINONE; RAC 4,4 DIMETHYL 3 (2 PHENYL 3 VINYLHEX 4 ENOYL) OXAZOLIDIN 2 ONE; RAC 4,4 DIMETHYL 3 (3 METHYL 2 PHENYLHEX 4 ENOYL) OXAZOLIDIN2 ONE; RAC 4,4 DIMETHYL 3 (3 PHENYL 2 THIOPHEN 3 YL PENT 4 ENOYL) OXAZOLIDIN 2 ONE; RAC 4,4 DIMETHYL 3 (4 METHYL 2 PHENYL 3 (TRIPHENYLSILYLOXY)PENTANOYL)OXAZOLIDIN 2 ONE; RAC 4,4 DIMETHYL 3 [2 (1 PHENYLALLYL) OCTANYL] OXAZOLIDIN 2 ONE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYSIS; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 77955661590     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.05.045     Document Type: Article

References (46)

1. (a) R. Mahrwald, Modern Aldol Reactions 2004 Wiley-VCH Weinheim, Germany
2. (b) T. Mukaiyama Org. React. 28 1982 203
3. (c) C.J. Cowden, and I. Paterson Org. React. 51 1997 1
4. (d) B.M. Kim, S.F. Williams, and S. Masamune B.M. Trost, Comprehensive Organic Synthesis 1991 Pergamon London
5. (e) D.A. Evans, J.V. Nelson, and T.R. Taber Top. Stereochem. 13 1982 1
6. For reviews see: (a) M. Shibasaki Multimetallic Catalysis in Organic Synthesis 2004 Wiley-VCH Weinhem
7. (b) M. Shibasaki, and N. Yoshikawa Chem. Rev. 102 2002 2187
8. (c) J.S. Johnson, and D.A. Evans Acc. Chem. Res. 33 2000 325
9. (d) For recent examples, please see M. Shibasaki, H. Sasai, and T. Arai Angew. Chem., Int. Ed. 36 1997 1236
10. (e) B.M. Trost, and C. Müller J. Am. Chem. Soc. 130 2008 2438 and references therein
11. (f) A.B. Northrup, and D.W.C. MacMillan J. Am. Chem. Soc. 124 2002 6798
12. For examples of multi-catalytic systems, see: (a) T.A. Cernak, and T.H. Lambert J. Am. Chem. Soc. 131 2009 3124
13. (b) B.D. Kelly, J.M. Allen, R.E. Tundel, and T.H. Lambert Org. Lett. 11 2009 1381
14. (c) P.A. Evans, J. Cui, S.J. Gharpure, and R.J. Hinkle J. Am. Chem. Soc. 125 2003 11456
15. (a) T. Suzuki, M. Tokunaga, and Y. Wakatsuki Org. Lett. 3 2001 735
16. (b) L. Ackermann, and L.T. Kaspar J. Org. Chem. 72 2007 6149
17. (c) J.M. Clay, and E. Vedejs J. Am. Chem. Soc. 127 2005 5766
18. (d) G.W. Kabalka, T.M. Shoup, and N.M. Goudgaon J. Org. Chem. 54 1989 5930
19. (e) Y. Chen, D.M. Ho, and C. Lee J. Am. Chem. Soc. 127 2005 12184
20. (f) N. Marion, R. Ramon, and S.P. Nolan J. Am. Chem. Soc. 131 2009 448
21. C.A. Witham, P. Mauleon, N.D. Shapiro, B.D. Sherry, and F.D. Toste J. Am. Chem. Soc. 129 2007 5838
22. For examples, see: (a) N. Saito, T. Katayama, and Y. Sato Org. Lett. 10 2008 3829
23. (b) B. Gourdet, and H.W. Lam J. Am. Chem. Soc. 131 2009 3802
24. (c) J.P. Das, H. Chechlik, and I. Marek Nat. Chem. 1 2009 128
25. For a review of ynamide chemistry: C.A. Zificsak, J.A. Mulder, R.P. Hsung, C. Rameshkumar, and L.L. Wei Tetrahedron 57 2001 7575
26. H. Yamamoto, and K. Futatsugi Angew. Chem., Int. Ed. 44 2005 1924
27. J. Sun, and S.A. Kozmin Angew. Chem., Int. Ed. 45 2006 4991
28. See Supplementary data for details.
29. (a) D.A. Evans, J.S. Tedrow, J.T. Shaw, and C.W. Downey J. Am. Chem. Soc. 124 2002 392
30. (b) D.A. Evans, C.W. Downey, J.T. Shaw, and J.S. Tredow Org. Lett. 4 2002 1127
31. (c) S. Saito, and S. Kobayashi J. Am. Chem. Soc. 128 2006 8704
32. (a) J. Ficini, N. Lumbroso-Bader, and J. Pouliquen Tetrahedron Lett. 39 1968 4139
33. (b) J. Ficini, and C. Barbara Tetrahedron Lett. 52 1966 6425
34. (c) A.M. Martin Castro Chem. Rev. 104 2004 2939
35. J.A. Mulder, R.P. Hsung, M.O. Frederick, M.R. Tracey, and C.A. Zificsak Org. Lett. 4 2002 1383
36. As the metal triflate catalyst controls the release of TfOH (see Experimental for details) it is possible that the reaction is catalyzed solely by the Brønsted acid. However, the use of solely catalytic amounts of TfOH only provides the rearranged product in <10% yield (cf. 88% with the catalytic metal triflate).
37. For recent examples of catalytic [3,3]-Claisen-type rearrangements, see: (a) S.G. Nelson, and K. Wang J. Am. Chem. Soc. 128 2006 4232
38. (b) D. Bourgeois, D. Craig, N.P. King, and D.M. Mountford Angew. Chem., Int. Ed. 44 2004 618
39. (c) K. Akiyama, and K. Mikami Tetrahedron Lett. 45 2004 7217
40. (d) B.D. Sherry, and F.D. Toste J. Am. Chem. Soc. 126 2004 15978
41. (e) S.G. Nelson, C.J. Bungard, and K. Wang J. Am. Chem. Soc. 125 2003 13000
42. (f) M. Hiersemann, and L. Abraham Eur. J. Org. Chem. 2002 1461
43. (g) C. Uyeda, and E. Jacobsen J. Am. Chem. Soc. 130 2008 9228
44. (h) E.C. Linton, and M.C. Kozlowski J. Am. Chem. Soc. 130 2008 16162
45. (i) T.P. Yoon, V.M. Dong, and D.W.C. MacMillan J. Am. Chem. Soc. 121 1999 9726
46. M.O. Frederick, J.A. Mulder, M.R. Tracey, R.P. Hsung, J. Huang, K.C.M. Kurtz, L. Shen, and C.J. Douglas J. Am. Chem. Soc. 125 2003 2368