Enantioselective iminium-catalyzed epoxidation of hindered trisubstituted allylic alcohols

Tetrahedron Asymmetry

Volumn 21, Issue 11-12, 2010, Pages 1611-1618

  Novikov, Roman ^a   Lacour, Jérôme ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

3,3 DIMETHYLBUTYL 2 AMINE; 5,5',6,6',7,7',8,8' OCTAHYDROBINAPHTHYL; ACETONITRILE; ALCOHOL; ALKENE; AMINE; CATION; DICHLOROMETHANE; HYDROXYL GROUP; IMINE; IMINIUM; UNCLASSIFIED DRUG;

ALLYLIC REARRANGEMENT; ARTICLE; CATALYST; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOSELECTIVITY; EPOXIDATION; PRIORITY JOURNAL; SUBSTITUTION REACTION;

EID: 77956651671     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.06.002     Document Type: Article

References (78)

1. P. Besse , and H. Veschambre Tetrahedron 50 1994 8885
2. C. Bonini , and G. Righi Tetrahedron 58 2002 4981
3. A.H. Li , L.X. Dai , and V.K. Aggarwal Chem. Rev. 97 1997 2341
4. R.A. Johnson , and K.B. Sharpless I. Ojima, Catalytic Asymmetric Synthesis 2000 VCH New York
5. Y. Hoshino , and H. Yamamoto J. Am. Chem. Soc. 122 2000 10452
6. N. Murase , Y. Hoshino , M. Oishi , and H. Yamamoto J. Org. Chem. 64 1999 338
7. W. Zhang , A. Basak , Y. Kosugi , Y. Hoshino , and H. Yamamoto Angew. Chem., Int. Ed. 44 2005 4389
8. N. Makita , Y. Hoshino , and H. Yamamoto Angew. Chem., Int. Ed. 42 2003 941
9. W. Zhang , and H. Yamamoto J. Am. Chem. Soc. 129 2007 286
10. E.N. Jacobsen I. Ojima, Catalytic Asymmetric Synthesis 1993 VCH New York, N.Y.
11. Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H.; Eds.; Comprehensive Asymmetric Catalysis I-III, Vol. 2, 1999
12. T. Katsuki I. Ojima, Catalytic asymmetric synthesis 2000 VCH New York
13. Q.H. Xia , H.Q. Ge , C.P. Ye , Z.M. Liu , and K.X. Su Chem. Rev. 2005 1603
14. W. Adam , C.R. Saha-Möller , and P.A. Ganeshpure Chem. Rev. 101 2001 3499
15. O.A. Wong , and Y. Shi Chem. Rev. 108 2008 3958
16. D. Yang Acc. Chem. Res. 37 2004 497
17. M. Marigo , J. Franzen , T.B. Poulsen , W. Zhuang , and K.A. Jorgensen J. Am. Chem. Soc. 127 2005 6964
18. S. Lee , and D.W.C. MacMillan Tetrahedron 62 2006 11413
19. X. Wang , and B. List Angew. Chem., Int. Ed. 47 2008 1119
20. X. Wang , C.M. Reisinger , and B. List J. Am. Chem. Soc. 130 2008 6070
21. A. Berkessel Angew. Chem., Int. Ed. 47 2008 3677
22. A. Berkessel , B. Koch , C. Toniolo , M. Rainaldi , Q.B. Broxterman , and B. Kaptein Biopolymers 84 2006 90
23. D.R. Kelly , and S.M. Roberts Biopolymers 84 2006 74
24. G. Peris , C.E. Jakobsche , and S.J. Miller J. Am. Chem. Soc. 129 2007 8710
25. R. Helder , J.C. Hummelen , R.W.P.M. Laane , J.S. Wiering , and H. Wynberg Tetrahedron Lett. 1976 1831
26. H. Wynberg , and B. Greijdanus J. Chem. Soc., Chem. Commun. 1978 427
27. B. Lygo , and P.G. Wainwright Tetrahedron Lett. 39 1998 1599
28. E.J. Corey , and F.Y. Zhang Org. Lett. 1 1999 1287
29. B. Lygo , and D.C.M. To Tetrahedron Lett. 42 2001 1343
30. S. Arai , H. Tsuge , M. Oku , M. Miura , and T. Shioiri Tetrahedron 58 2002 1623
31. T. Ooi , D. Ohara , M. Tamura , and K. Maruoka J. Am. Chem. Soc. 126 2004 6844
32. A. Berkessel , M. Guixà , F. Schmidt , J.M. Neudörfl , and J. Lex Chem. Eur. J. 13 2007 4483
33. G. Hanquet , and X. Lusinchi Tetrahedron Lett. 34 1993 5299
34. L. Bohé , M. Lusinchi , and X. Lusinchi Tetrahedron 55 1999 155
35. A. Gluszynska , I. Mackowska , M.D. Rozwadowska , and W. Sienniak Tetrahedron: Asymmetry 15 2004 2499
36. R.E. delRio , B. Wang , S. Achab , and L. Bohé Org. Lett. 9 2007 2265
37. G. Hanquet , X. Lusinchi , and P. Milliet C.R. Acad. Sci., Ser. II: Mec., Phys., Chim., Sci. Terre Univers 313 1991 625
38. X. Lusinchi , and G. Hanquet Tetrahedron 53 1997 13727
39. L. Bohé , G. Hanquet , M. Lusinchi , and X. Lusinchi Tetrahedron Lett. 34 1993 7271
40. P.C.B. Page , G.A. Rassias , D. Bethell , and M.B. Schilling J. Org. Chem. 63 1998 2774
41. A. Armstrong , G. Ahmed , I. Garnett , K. Goacolou , and J.S. Wailes Tetrahedron 55 1999 2341
42. S. Minakata , A. Takemiya , K. Nakamura , I. Ryu , and M. Komatsu Synlett 2000 1810
43. P.C.B. Page , G.A. Rassias , D. Barros , D. Bethell , and M.B. Schilling J. Chem. Soc., Perkin Trans. 1 2000 3325
44. P.C.B. Page , G.A. Rassias , D. Barros , A. Ardakani , B. Buckley , D. Bethell , T.A.D. Smith , and A.M.Z. Slawin J. Org. Chem. 66 2001 6926
45. M.-K. Wong , L.-M. Ho , Y.-S. Zheng , C.-Y. Ho , and D. Yang Org. Lett. 3 2001 2587
46. P.C.B. Page , G.A. Rassias , D. Barros , A. Ardakani , D. Bethell , and E. Merifield Synlett 2002 580
47. P.C.B. Page , B.R. Buckley , H. Heaney , and A.J. Blacker Org. Lett. 7 2005 375
48. P.C.B. Page , D. Barros , B.R. Buckley , and B.A. Marples Tetrahedron: Asymmetry 16 2005 3488
49. P.C.B. Page , B.R. Buckley , G.A. Rassias , and A.J. Blacker Eur. J. Org. Chem. 2006 803
50. J. Lacour , D. Monchaud , and C. Marsol Tetrahedron Lett. 43 2002 8257
51. P.C.B. Page , D. Barros , B.R. Buckley , A. Ardakani , and B.A. Marples J. Org. Chem. 69 2004 3595
52. J. Vachon , C. Pérollier , D. Monchaud , C. Marsol , K. Ditrich , and J. Lacour J. Org. Chem. 70 2005 5903
53. V.K. Aggarwal , and M.F. Wang Chem. Commun. 1996 191
54. J. Vachon , C. Lauper , K. Ditrich , and J. Lacour Tetrahedron: Asymmetry 17 2006 2334
55. P.C.B. Page , M.M. Farah , B.R. Buckley , and A.J. Blacker J. Org. Chem. 72 2007 4424
56. J. Vachon , S. Rentsch , A. Martinez , C. Marsol , and J. Lacour Org. Biomol. Chem. 5 2007 501
57. R. Novikov , J. Vachon , and J. Lacour Chimia 61 2007 236
58. R. Novikov , G. Bernardinelli , and J. Lacour Adv. Synth. Catal. 350 2008 1113
59. P.C.B. Page , R. Buckley Benjamin , and A.J. Blacker Org. Lett. 6 2004 1543
60. P.C.B. Page , B.R. Buckley , D. Barros , A.J. Blacker , B.A. Marples , and M.R.J. Elsegood Tetrahedron 63 2007 5386
61. R. Novikov , G. Bernardinelli , and J. Lacour Adv. Synth. Catal. 351 2009 596
62. Compounds 1a and 1b have predominantly anti- and syn-periplanar conformations, respectively.
63. TRISPHAT stands for tris(tetrachlorobenzenediolato)phosphate(V).
64. F. Favarger , C. Goujon-Ginglinger , D. Monchaud , and J. Lacour J. Org. Chem. 69 2004 8521
65. J. Lacour , C. Ginglinger , C. Grivet , and G. Bernardinelli Angew. Chem., Int. Ed. 36 1997 608
66. P.C.B. Page , B.R. Buckley , D. Barros , A.J. Blacker , H. Heaney , and B.A. Marples Tetrahedron 62 2006 6607
67. 6] are necessary with electron-rich olefins such as S9 (5 mol %) in comparison with its more electron-poor analogue S8 (10 mol %).
68. Enantiomeric ratios have been calculated from the original chromatographic data.
69. In the test reaction, the epoxidation reaction of S10 (0.2 mmol, 41 mg) was performed using 5 mol % of iminium catalyst which led after 24 h to a clean and full conversion of the allylic alcohol to the epoxide (81% yield, 85% ee).
70. D. Yang , M.K. Wong , and Y.C. Yip J. Org. Chem. 60 1995 3887
71. M.-H. Gonçalves , A. Martinez , S. Grass , P.C.B. Page , and J. Lacour Tetrahedron Lett. 47 2006 5297
72. 6] possess a limited solubility in dichloromethane above 20 mol %.
73. G.A. Pinna , G. Cignarella , S. Ruiu , G. Loriga , G. Murineddu , S. Villa , G.E. Grella , G. Cossu , and W. Fratta Bioorg. Med. Chem. 11 2003 4015
74. N. Imai , T. Noguchi , J. Nokami , and J. Otera Okayama Rika Daigaku Kiyo, A: Shizen Kagaku 39A 2003 47
75. A. Srikrishna , and P.P. Kumar Tetrahedron Lett. 36 1995 6313
76. K. Tanaka , and G.C. Fu J. Org. Chem. 66 2001 8177
77. Z.X. Wang , and Y. Shi J. Org. Chem. 63 1998 3099
78. P. Sjo , and A.J. Aasen Acta Chem. Scand. 47 1993 486