Enantioselective and regioselective nickel-catalyzed multicomponent coupling of chiral allenes, aromatic aldehydes, and silanes

Tetrahedron

Volumn 61, Issue 48, 2005, Pages 11405-11417

  Ng, Sze Sze ^a   Jamison, Timothy F ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Allene; Asymmetric catalysis; Chirality transfer; N Heterocyclic carbene; Nickel

Indexed keywords

ALDEHYDE DERIVATIVE; ALLENE DERIVATIVE; NICKEL; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 27444447789     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.08.063     Document Type: Article

References (62)

1. J. Zhu H. Bienaymé Multicomponent Reactions 2005 Wiley-VCH Weinheim
2. D.J. Ramón, and M. Yus Angew. Chem., Int. Ed. 44 2005 1602 1634
3. Nickel: (a) E. Oblinger, and J. Montgomery J. Am. Chem. Soc. 119 1997 9065 9066
4. W.-S. Huang, J. Chan, and T.F. Jamison Org. Lett. 2 2000 4221 4223
5. K.M. Miller, W.-S. Huang, and T.F. Jamison J. Am. Chem. Soc. 125 2003 3442 3443
6. (b) Review: J. Montgomery J. Angew. Chem., Int. Ed. 43 2004 3890 3908
7. (e) Rhodium: H.-Y. Jang, R.R. Huddleston, and M.J. Krische J. Am. Chem. Soc. 126 2004 4664 4668
8. C. Molinaro, and T.F. Jamison J. Am. Chem. Soc. 125 2003 8076 8077
9. S.J. Patel, and T.F. Jamison Angew. Chem., Int. Ed. 42 2003 1364 1367
10. S.J. Patel, and T.F. Jamison Angew. Chem., Int. Ed. 43 2004 3941 3944
11. Ng, S.-S.; Jamison, T. F., J. Am. Chem. Soc. 2005, 127, 7320-7321.
12. U. Anwar, R. Grigg, M. Rasparini, and V. Sridharan Chem. Commun. 2000 645 646
13. Y.-H. Ha, and S.-K. Kang Org. Lett. 4 2002 1143 1146
14. C.D. Hopkins, and H.C. Malinakova Org. Lett. 6 2004 2221 2224
15. J. Montgomery, and M. Song Org. Lett. 4 2002 4009 4011
16. S.-K. Kang, and S.-K. Yoon Chem. Commun. 2002 2634 2635
17. M.-S. Wu, D.K. Rayabarapu, and C.-H. Cheng J. Am. Chem. Soc. 125 2003 12426 12427
18. N. Krause A.S.K. Hashmi Modern Allene Chemistry Vol. 1-2 2004 Wiley-VCH Weinheim
19. R.L. Danheiser, and D.J. Carini J. Org. Chem. 45 1980 3925 3929
20. M. Ishiguro, N. Ikeda, and H. Yamamoto J. Org. Chem. 47 1982 2225 2227
21. J.A. Marshall Chem. Rev. 100 2000 3163 3186
22. D.R. Taylor, and D.B. Wright J. Chem. Soc., Perkin Trans. 1 1973 956 959
23. B.M. Trost, A.B. Pinkerton, and M. Seidel J. Am. Chem. Soc. 121 1999 10842 10843
24. A. Holemann, and H.-U. Reissig Org. Lett. 5 2003 1463 1466
25. M. Takimoto, M. Kawamura, and M. Mori Org. Lett. 5 2003 2599 2601
26. F.-Y. Yang, M. Shanmugasundaram, S.-Y. Chuang, P.-J. Ku, M.-Y. Wu, and C.-H. Cheng J. Am. Chem. Soc. 123 2003 12576 12583
27. M. Takimoto, M. Kawamura, and M. Mori Synthesis 2004 791 795
28. Coupling of the allene sp carbon with carbonyl groups is much more common in intramolecular reactions, where geometric constraints of ring closure play a substantial role. See Vol. 2 of Ref. 7 for examples.
29. See Ref. 6c for an isolated example of highly enantioselective coupling, and Refs. 7 and 8c for enantioselective allenylmetal addition.
30. For examples of Ni-catalyzed multi-component coupling reactions of allenes, see Ref. 6d-f and (a) N. Satyanarayana, H. Alper, and I. Amer Organometallics 9 1990 284 286
31. M.-S. Wu, D.K. Rayabarapu, and C.-H. Cheng J. Am. Chem. Soc. 125 2003 12426 12427
32. Established by NOE experiments and comparison to related Z and E allylic alcohols: (a) A. Inoue, K. Kitagawa, H. Shinokubo, and K. Oshima J. Org. Chem. 66 2001 4333 4339
33. E.A. Colby, and T.F. Jamison J. Org. Chem. 68 2003 156 166
34. Review: W.A. Herrmann Angew. Chem., Int. Ed. 41 2002 1290 1309
35. G.M. Mahandru, G. Liu, and J. Montgomery J. Am. Chem. Soc. 126 2004 3698 3699
36. R. Sawaki, Y. Sato, and M. Mori Org. Lett. 6 2004 1131 1133
37. In the case of 2,3-nonadiene ('methyl vs n-hexyl'), 1:1 site selectivity was observed, but the allylic:homoallylic selectivity was 93:7, and the Z/E ratio of the allylic product was >95:5, as observed in all other cases. See Section 7 for details.
38. See Section 7 and (a) J.M. Brown, and D. Parker Tetrahedron Lett. 22 1981 2815 2818
39. I. Fleming, G.R. Jones, N.D. Kindon, Y. Landais, C.P. Leslie, I.T. Morgan, S. Peukert, and A.K. Sarkar J. Chem. Soc., Perkin Trans. 1 1996 1171 1196
40. R. Gibbs, K. Bartels, R.W.K. Lee, and W.H. Ojamura J. Am. Chem. Soc. 111 1989 3717 3725
41. M.S. Shepard, and E.M. Carreira J. Am. Chem. Soc. 119 1997 2597 2605
42. P.A. Wender, F. Glorius, C.O. Husfeld, E. Langkopf, and J.A. Love J. Am. Chem. Soc. 121 1999 5348 5349
43. H. Hu, D. Smith, R.E. Cramer, and M.A. Tius J. Am. Chem. Soc. 121 1999 9895 9896
44. W.L. Waters, W.S. Linn, and M.C. Caserio J. Am. Chem. Soc. 90 1968 6741 6749
45. I. Ikeda, K. Honda, E. Osawa, M. Shiro, M. Aso, and K. Kanematsu J. Org. Chem. 61 1996 2031 2037
46. S. Ma, H. Ren, and Q. Wei J. Am. Chem. Soc. 125 2003 4817 4830
47. A.J. Arduengo III, R. Krafczyk, and R. Schmutzler Tetrahedron 55 1999 14523 14534
48. A.E. Finholt, A.C. Bond Jr., K.E. Wilzboch, and H.I. Schlessinger J. Am. Chem. Soc. 69 1947 2692 2696
49. K. Burgess, and L.D. Jennings J. Am. Chem. Soc. 113 1991 6129 6139
50. J.A. Dale, D.L. Dull, and H.S. Mosher J. Org. Chem. 34 1969 2543 2549
51. J.A. Dale, and H.S. Mosher J. Am. Chem. Soc. 95 1973 512 519
52. N.A. Yakelis, and W.R. Roush J. Org. Chem. 68 2003 3838 3843
53. A.G. Myers, and B. Zheng J. Am. Chem. Soc. 118 1996 4492 4493
54. (b) Myers, A. G.; Zheng, B. Org. Synth. 1998, 76, 178-188.
55. A.G. Myers, B. Zheng, and M. Movassaghi J. Org. Chem. 62 1997 7507
56. E.L. Eliel, S.H. Wilen, and L.N. Mander Stereochemistry of Organic Compounds 1994 Wiley New York p 1091
57. R.L. Danheiser, Y.M. Choi, M. Menichincheri, and E.J. Stoner J. Org. Chem. 58 1993 322 327
58. D.J. Pasto, and J.E. Brophy J. Org. Chem. 56 1991 4554 4556
59. F.E. Michael, A.P. Duncan, Z.K. Sweeney, and R.G. Bergman J. Am. Chem. Soc. 125 2003 7184 7185
60. J.M. Brown, and D. Parker Tetrahedron Lett. 22 1981 2815 2818
61. D. Parker J. Chem. Soc., Perkin Trans. 2 1983 83 88
62. I. Fleming, G.R. Jones, N.D. Kindon, Y. Landais, C.P. Leslie, I.T. Morgan, S. Peukert, and A.K. Sarkar J. Chem. Soc., Perkin Trans. 1 1996 1171 1196