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Synlett 2003(4): 0561-0563
DOI: 10.1055/s-2003-37527
DOI: 10.1055/s-2003-37527
LETTER
© Georg Thieme Verlag Stuttgart · New York
Optically Active Lithium-Alkoxide Catalyzed Asymmetric Reduction of Imines with Trimethoxyhydrosilane
Further Information
Received
19 January 2003
Publication Date:
26 February 2003 (online)
Publication History
Publication Date:
26 February 2003 (online)
Abstract
Optically active lithium alkoxide catalyzed asymmetric reduction of imines with trimethoxhydroysilane in moderate enantioselectivity (up to 72% ee).
Key words
asymmetric reduction - lithium alkoxide - imine - solvent effect
- 1 For the review of asymmetric hydrosilylation,
see for example:
Nishiyama H.Itoh K. In Catalytic Asymmetric Synthesis 2nd ed.:Ojima I. VCH Publisher, Inc.; New York: 2000. p.111 - For reviews of extracoordination at silicon, see:
-
2a
Brook MA. Silicon in Organic, Organometallic, and Polymer Chemistry Interscience Publisher, Inc.; New York: 2000. Chap. 4. p.97 -
2b
Hosomi A. Reviews on Heteroatom Chemistry 1992, 7: 214 - 3
Hosomi A.Hayashida H.Kohra S.Tominaga Y. J. Chem. Soc., Chem. Commun. 1986, 1411 -
4a
Kohra S.Hayashida H.Tominaga Y.Hosomi A. Tetrahedron Lett. 1988, 29: 89 -
4b
Hojo M.Fujii A.Murakami C.Aihara H.Hosomi A. Tetrahedron Lett. 1995, 36: 571 -
5a
Pini D.Iuliano A.Salvadori P. Tetrahedron: Asymmetry 1992, 3: 693 -
5b
Schiffers R.Kagan HB. Synlett 1997, 1175 -
5c
LaRonde FJ.Brook MA. Tetrahedron Lett. 1999, 40: 3507 - 6
Hojo M.Murakami C.Fujii A.Hosomi A. Tetrahedron Lett. 1999, 40: 911 - 7 Matsumura et al. reported proline
derivatives catalyzed asymmetric reduction with trichlorosilane
and moderate enantioselectivity of 66% ee was achieved:
Iwasaki F.Onomura O.Mishima K.Kanematsu T.Maki T.Matsumura Y. Tetrahedron Lett. 2001, 42: 2525
References
We have already found that diastereoselectivity was switched by selection of solvent in the reduction of α,β-epoxyketones. See ref. [4b]