Regio- and stereoselective preparation of highly substituted tertiary homoallylic alcohols

Tetrahedron Letters

Volumn 52, Issue 35, 2011, Pages 4575-4578

  Takeda, Takeshi ^a   Wasa, Hideki ^a   Tsubouchi, Akira ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

Silyl allylic sulfides; Substituted homoallylic alcohols; Cross coupling; Multi stereogenic centers; Titanocene(II)

Indexed keywords

ALCOHOL DERIVATIVE; ALPHA(BENZYLDIMETHYLSILYL)ALLYLIC SULFIDE; BETA DELTA DISUBSTITUTED TERTIARY HOMOALLYLIC ALCOHOL; DELTA SILYLHOMOALLYLIC ALCOHOL; DISULFIDE; HALIDE; HOMOALLYLIC ALCOHOL; KETONE; PALLADIUM COMPLEX; TITANOCENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CROSS COUPLING REACTION; REGIOSELECTIVITY; STEREOCHEMISTRY;

EID: 79960967067     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.06.111     Document Type: Article

References (28)

1. N. Risch, and M. Arend G. Helmchen, R. Hoffmann, J. Mulzer, E. Schaumann, Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl) vol. 3 1996 Thieme Stuttgart 1357
2. S.E. Denmark, and N.G. Almstead J. Otera, Modern Carbonyl Chemistry 2000 Wiley-VCH Weinheim Chapter 10
3. S.R. Chemler, and W.R. Roush J. Otera, Modern Carbonyl Chemistry 2000 Wiley-VCH Weinheim Chapter 11
4. J. Szymoniak, and C. Moïse I. Marek, Titanium and Zirconium in Organic Synthesis 2002 Wiley-VCH Weinheim Chapter 13
5. A.B. Santanilla, and J.L. Leighton J.G. De Vries, G.A. Molander, P.A. Evans, Science of Synthesis Vol. 2 2011 Thieme Stuttgart 401
6. Y. Yatsumonji, T. Nishimura, A. Tsubouchi, K. Noguchi, and T. Takeda Chem. Eur. J. 15 2009 2680
7. T. Takeda, T. Nishimura, Y. Yatsumonji, K. Noguchi, and A. Tsubouchi Chem. Eur. J. 16 2010 4729
8. Precedent works for the preparation of allyltitanium compounds and their diastereoselective addition to carbonyls, see: M.T. Reetz Organotitanium Reagents in Organic Synthesis 1986 Springer Berlin Chapter 5
9. F. Sato, H. Urabe, and S. Okamoto Chem. Rev. 100 2000 2835
10. R. Wada, K. Oisaki, M. Kanai, and M. Shibasaki J. Am. Chem. Soc. 126 2004 8910
11. L. Carosi, and D.G. Hall Angew. Chem., Int. Ed. 46 2007 5913
12. H. Lachance, and D.G. Hall Org. React. 73 2008 1
13. U. Schneider, M. Ueno, and S. Kobayashi J. Am. Chem. Soc. 130 2008 13284
14. F. Nowrouzi, A. Thadani, and R.A. Batey Org. Lett. 11 2009 2631
15. M. Yasuda, K. Hirata, A. Nishino, A. Yamamoto, and A. Baba J. Am. Chem. Soc. 124 2002 13442
16. L.F. Tietze, T. Knizel, and S. Schmatz J. Am. Chem. Soc. 128 2006 11483
17. H. Ren, G. Dunet, P. Mayer, and P. Knochel J. Am. Chem. Soc. 129 2007 5376
18. G. Dunet, P. Mayer, and P. Knochel Org. Lett. 10 2008 117
19. B. Dutta, N. Gilboa, and I. Marek J. Am. Chem. Soc. 132 2010 5588
20. M. Yamaguchi, and T. Mukaiyama Chem. Lett. 1980 993
21. R.W. Hoffmann, and T. Sander Chem. Ber. 123 1990 145
22. G.Y. Fang, and V.K. Aggarwal Angew. Chem., Int. Ed. 46 2007 359
23. M. Althaus, A. Mahmood, J.R. Suárez, S.P. Thomas, and V.K. Aggarwal J. Am. Chem. Soc. 132 2010 4025
24. E.S. Schmidtmann, and M. Oestreich Angew. Chem., Int. Ed. 48 2009 4634
25. A.N. Kasatkin, and R.J. Whitby Tetrahedron Lett. 40 1999 9353
26. K. Takaki, T. Kusudo, S. Uebori, T. Nishiyama, T. Kamata, M. Yokoyama, K. Takehira, Y. Makioka, and Y. Fujiwara J. Org. Chem. 63 1998 4299
27. T. Shono, Y. Hayata, A. Tsubouchi, and T. Takeda Tetrahedron Lett. 47 2006 1257
28. B.M. Trost, M.R. Machacek, and Z.T. Ball Org. Lett. 5 2003 1895