On the stereochemical course of the addition of allylsilanes to aldehydes

Tetrahedron

Volumn 68, Issue 37, 2012, Pages 7701-7718

  Denmark, Scott E ^a   Weber, Eric J ^a   Almstead, Neil G ^a   Wolf, Larry M ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

Aldehyde; Allylsilane; Antiperiplanar; Lewis acid; Stereochemistry; Synclinal

Indexed keywords

ALDEHYDE; LEWIS ACID; SILANE DERIVATIVE;

CONFERENCE PAPER; CONTROLLED STUDY; CYCLIZATION; PRIORITY JOURNAL; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 84864419634     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.05.084     Document Type: Conference Paper

References (108)

1. R.W. Hoffmann Angew. Chem., Int. Ed. Engl. 26 1987 489 503
2. Y. Yamamoto, and N. Asao Chem. Rev. 93 1993 2207 2293
3. G. Helmchen, R. Hoffmann, J. Mulzer, and E. Schaumann Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl); E21 Vol. 3 1996 Thieme Stuttgart 1357 1602
4. S.R. Chemler, and W.R. Roush J. Otera, Modern Carbonyl Chemistry 2000 Wiley-VCH Weinheim Chapter 11
5. A. Yanagisawa E.N. Jacobsen, A. Pfaltz, H. Yamamoto, Comprehensive Asymmetric Catalysis vol. 2 1999 Springer Berlin Chapter 27
6. S.E. Denmark, and N.G. Almstead J. Otera, Modern Carbonyl Chemistry 2000 Wiley-VCH Weinheim Chapter 10
7. S.E. Denmark, and J. Fu Chem. Rev. 103 2003 2763 2793
8. M. Yus, J.C. Gonzalez-Gomez, and F. Foubelo Chem. Rev. 111 2011 7774 7854
9. To effectively describe the products observed in these reactions the stereochemical descriptors suggested by Masamune will be employed: S. Masamune, T. Kaiko, and D.S. Garvey J. Am. Chem. Soc. 104 1982 5521 5523
10. R.W. Hoffmann B.M. Trost, Stereocontrolled Organic Synthesis 1994 Blackwell Scientific Publications Cambridge 259 274
11. W.R. Roush G. Helmchen, R.W. Hoffmann, J. Mulzer, E. Schaumann, Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl); E21 Vol. 3 1996 Thieme Stuttgart New York 1410 1486
12. D.G. Hall, and H. Lachance Org. React. 73 2008 1 573
13. B.W. Gung Org. React. 64 2004 1 413
14. Y. Yamamoto Acc. Chem. Res. 20 1987 243 249
15. H. Sakurai Pure Appl. Chem. 54 1982 1 22
16. G. Majetich Organic Synthesis T. Hudlicky, Theory and Applications Vol. 1 1989 JAI Greenwich 173 240
17. A. Hosomi Acc. Chem. Res. 21 1988 200 206
18. I. Fleming, J. Dunogués, and R. Smithers Org. React. 37 1989 57 575
19. I. Fleming, A. Barbero, and D. Walter Chem. Rev. 97 1997 2063 2192
20. E. Langkopf, and D. Schinzer Chem. Rev. 95 1995 1375 1408
21. C.E. Masse, and J.S. Panek Chem. Rev. 95 1995 1293 1316
22. The intramolecular reactions of allylsilanes have also been reviewed D. Schinzer Synthesis 1988 263 273
23. A. Furstner Chem. Rev. 99 1999 991 1045
24. P. Cintas Synthesis 1992 248 257
25. M. Avalos, R. Babiano, P. Cintas, J.L. Jimenez, and J.C. Palacios Chem. Soc. Rev. 28 1999 169 177
26. G.C. Hargaden, and P.J. Guiry Adv. Synth. Catal. 349 2007 2407 2424
27. R.O. Duthaler, and A. Hafner Chem. Rev. 92 1992 807 832
28. R.O. Duthaler, A. Hafner, P.L. Alsters, P. Rothe-Streit, and G. Rihs Pure Appl. Chem. 64 1992 1897 1910
29. D. Hoppe Stereoselective Synthesis G. Helmchen, R.W. Hoffmann, J. Mulzer, E. Schaumann, 1995 Thieme Stuttgart: New York 1551 1583 Vol. E 21b
30. S.E. Denmark, and E.J. Weber Helv. Chim. Acta 66 1983 1655 1660
31. For an early, general discussion of the topological features of reactions of double bonds see: D. Seebach, and J. Golinski Helv. Chim. Acta 64 1981 1413 1423
32. S.E. Denmark, and E.J. Weber J. Am. Chem. Soc. 106 1984 7970 7971
33. S.E. Denmark, B.R. Henke, and E.J. Weber J. Am. Chem. Soc. 109 1987 2512 2514
34. S.E. Denmark, E.J. Weber, T.M. Wilson, and T.M. Willson Tetrahedron 45 1989 1053 1065
35. S.E. Denmark, and N.G. Almstead J. Org. Chem. 59 1994 5130 5132
36. S.E. Denmark, and S. Hosoi J. Org. Chem. 59 1994 5133 5135
37. S.E. Denmark, and N.G. Almstead J. Mex. Chem. Soc. 53 2009 174 192
38. M. Imachi, J. Nakagawa, and M. Hayashi J. Mol. Struct. 102 1983 403 412
39. M. Hayashi, M. Imachi, and M. Saito Chem. Lett. 1977 221 222
40. B. Beagley, A. Foord, R. Moutran, and B. Roszondai J. Mol. Struct. 1977 117 120
41. K. Ohno, K. Toga, and M. Murata Bull. Chem. Soc. Jpn. 50 1977 2870 2876
42. J.M. White, and C.I. Clark S.E. Denmark, Topics in Stereochemistry 1999 Wiley New York 137 200
43. S.D. Kahn, C.F. Pau, A.R. Chamberlin, and W.J. Hehre J. Am. Chem. Soc. 109 1987 650 663
44. V.G. Matassa, P.R. Jenkins, A. Kümin, L. Damm, J. Schreiber, D. Felix, E. Zass, and A. Eschenmoser Isr. J. Chem. 29 1989 321 343
45. S.E. Denmark, and N.S. Werner J. Am. Chem. Soc. 132 2010 3612 3620
46. I. Fleming, and N.K. Terrett Pure Appl. Chem. 55 1983 1707 1713
47. I. Fleming Pure Appl. Chem. 60 1988 71 78
48. M.J. Carter, and I. Fleming J. Chem. Soc., Chem. Commun. 1976 679 680
49. B.-W. Au-Yeung, and I. Fleming J. Chem. Soc., Chem. Commun. 1977 79 80
50. B.-W. Au-Yeung, and I. Fleming J. Chem. Soc., Chem. Commun. 1977 81
51. I. Fleming, and R.V. Williams J. Chem. Soc., Perkin Trans. 1 1981 684 688
52. M.J. Carter, I. Fleming, and A. Percival J. Chem. Soc., Perkin Trans. 1 1981 2415 2434
53. T.H. Chan, and I. Fleming Synthesis 1979 761 786
54. I. Fleming, and B.-W. Au-Yeung Tetrahedron 37 1981 13 24
55. I. Fleming, and N.K. Terrett Tetrahedron Lett. 25 1984 5103 5104
56. I. Fleming, and N.K. Terrett J. Organomet. Chem. 264 1984 99 118
57. I. Fleming, and N.K. Terrett Tetrahedron Lett. 24 1983 4153 4156
58. H.-F. Chow, and I. Fleming Tetrahedron Lett. 26 1985 397 400
59. I. Fleming, A.K. Sarkar, and A.P. Thomas J. Chem. Soc., Chem. Commun. 1987 157 159
60. H. Wetter, P. Scherer, and W.B. Schweizer Helv. Chim. Acta 62 1979 1985 1989
61. H. Wetter, and P. Scherer Helv. Chim. Acta 66 1983 118 122
62. D. Young, and W. Kitching Tetrahedron Lett. 24 1983 5793 5796
63. G. Wickham, and W. Kitching J. Org. Chem. 48 1983 612 614
64. G. Wickham, and W. Kitching Organometallics 2 1983 541 547
65. D. Young, W. Kitching, and G. Wickham Tetrahedron Lett. 24 1983 5789 5792
66. D. Young, and W. Kitching Aust. J. Chem. 38 1985 1767 1777
67. D. Young, M. Jones, and W. Kitching Aust. J. Chem. 39 1986 563 573
68. G. Wickham, D. Young, and W. Kitching Organometallics 7 1988 1187 1195
69. T. Hayashi, M. Konishi, and M. Kumada J. Am. Chem. Soc. 104 1982 4963 4965
70. T. Hayashi, M. Konishi, and M. Kumada J. Org. Chem. 48 1983 281 282
71. T. Hayashi, H. Ito, and N. Kumada Tetrahedron Lett. 23 1982 4605 4606
72. T. Hayashi, Y. Okamoto, K. Kabeta, T. Hagihara, and M. Kumada J. Org. Chem. 49 1984 4224 4226
73. S. Shambayati, W.E. Crowe, and S.L. Schreiber Angew. Chem., Int. Ed. Engl. 29 1990 256 272
74. T. Ooi, and K. Maruoka J. Otera, Modern Carbonyl Chemistry 2000 Wiley-VCH Weinheim Chapter 1
75. S. Saito, and H. Yamamoto J. Otera, Modern Carbonyl Chemistry 2000 Wiley-VCH Weinheim Chapter 2
76. M.T. Reetz, M. Hüllmann, W. Massa, S. Berger, P. Rademacher, and P. Heymanns J. Am. Chem. Soc. 108 1986 2405 2408
77. S.E. Denmark, and N.G. Almstead J. Am. Chem. Soc. 115 1993 3133 3139
78. G.E. Keck, and S. Castellino J. Am. Chem. Soc. 108 1986 3847 3849
79. G.E. Keck, S. Castellino, and M.R. Wiley J. Org. Chem. 51 1986 5478 5480
80. F. Filippini, and B.-P. Susz Helv. Chim. Acta 54 1971 835 845
81. I.R. Beattie Quart. Rev. 17 1963 382 405
82. M.M. Biddle, and H.J. Reich J. Org. Chem. 71 2006 4031 4039
83. D. Seyferth, and J. Pornet J. Org. Chem. 45 1980 1721 1722
84. D. Seyferth, J. Pornet, and R.M. Weinstein Organometallics 1 1982 1651 1658
85. A. Hosomi, M. Saito, and H. Sakurai Tetrahedron Lett. 21 1980 3783 3786
86. J.P. Schmidt, M. Piranx, and J.F. Phillete J. Org. Chem. 40 1975 1586 1588
87. L. Gruber, I. Tomoskozi, and L. Radies Synthesis 1975 708
88. K. Tamao, K. Sumitami, and M. Kumada J. Am. Chem. Soc. 94 1972 4374 4376
89. D. Pederson J. Org. Chem. 33 1968 780 784
90. M. Mokotoff, and R.C. Cavestri J. Org. Chem. 39 1974 409 411 and references cited therein
91. S. Krishnamurthy J. Org. Chem. 46 1981 4628 4829
92. The tert-butyldimethylsilyl ether was originally employed as the protecting group in the synthesis of 10, but this protecting group could not be removed without affecting the pentadienylsilyl moiety. The diphenylmethylsilyl ether was expressly developed for this purpose S.E. Denmark, R.P. Hammer, E.J. Weber, and K.L. Habermas J. Org. Chem. 52 1987 165 168
93. K. Narasaka, A. Morikawa, K. Saigo, and T. Mukaiyama Bull. Chem. Soc. Jpn. 50 1977 2773 2776
94. A.P. Kozikowski, and R.J. Schmiesing J. Org. Chem. 48 1983 1000 1007
95. K. Tamao, T. Kakui, M. Akita, T. Iwahara, R. Kanatani, J. Yoshida, and M. Kumada Tetrahedron 39 1983 983 990
96. W. Oppolzer, R.J. Mills, W. Pachinger, and T. Stevenson Helv. Chim. Acta 69 1986 1542 1545
97. W.E. Fristad, and J.R. Peterson J. Org. Chem. 50 1985 10 18
98. W.H. Pirkle, and P.E. Adams J. Org. Chem. 45 1980 4111 4117
99. J.B. Stothers, and C.T. Tan Can. J. Chem. 54 1976 917 925
100. R. Huisgen Acc. Chem. Res. 10 1977 117 124
101. C. Reichardt Solvent and Solvent Effects in Organic Chemistry 2nd ed. 1988 VCH Weinheim 363 376
102. N.T. Anh, and B.T. Thanh Nouv. J. Chim. 10 1986 681 683
103. J. Mulzer, G. Buntrup, J. Finke, and M. Zippel J. Am. Chem. Soc. 101 1979 7723 7725
104. Y. Zhao, and D.G. Truhlar Acc. Chem. Res. 41 2008 157 167
105. V. Barone, and M. Cossi J. Phys. Chem. A 102 1998 1995 2001
106. M.W. Schmidt, K.K. Baldridge, J.A. Boatz, S.T. Elbert, M.S. Gordon, J.H. Jensen, S. Koseki, N. Matsunaga, L.A. Nguyen, S. Su, T.L. Windus, M. Dupuis, and J.A. Montgomery J. Comput. Chem. 14 1993 1347 1363
107. W.C. Still, M. Kahn, and A. Mitra J. Org. Chem. 43 1978 2923 2925
108. H. Gilman, and F. Schulze J. Am. Chem. Soc. 47 1925 2002 2005