Optically active lithium-alkoxide catalyzed asymmetric reduction of imines with trimethoxyhydrosilane

Synlett

Volumn , Issue 4, 2003, Pages 561-563

  Nishikori, Hisashi ^a   Yoshihara, Ritsuko ^a   Hosomi, Akira ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

Asymmetric reduction; Imine; Lithium alkoxide; Solvent effect

Indexed keywords

IMINE; LITHIUM DERIVATIVE; SILANE DERIVATIVE; TRIMETHOXYHYDROSILANE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; OPTICAL ROTATION; REACTION ANALYSIS; REDUCTION; STRUCTURE ANALYSIS;

EID: 0037240055     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-37527     Document Type: Article

References (12)

1. For the review of asymmetric hydrosilylation, see for example: Nishiyama, H.; Itoh, K. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; VCH Publisher, Inc.: New York, 2000, 111.
2. For reviews of extracoordination at silicon, see: (a) Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry; Interscience Publisher, Inc.: New York, 2000, Chap. 4, 97. (b) Hosomi, A. Reviews on Heteroatom Chemistry 1992, 7, 214.
3. For reviews of extracoordination at silicon, see: (a) Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry; Interscience Publisher, Inc.: New York, 2000, Chap. 4, 97. (b) Hosomi, A. Reviews on Heteroatom Chemistry 1992, 7, 214.
4. Hosomi, A.; Hayashida, H.; Kohra, S.; Tominaga, Y. J. Chem. Soc., Chem. Commun. 1986, 1411.
5. (a) Kohra, S.; Hayashida, H.; Tominaga, Y.; Hosomi, A. Tetrahedron Lett. 1988, 29, 89.
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7. (a) Pini, D.; Iuliano, A.; Salvadori, P. Tetrahedron: Asymmetry 1992, 3, 693.
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9. (c) LaRonde, F. J.; Brook, M. A. Tetrahedron Lett. 1999, 40, 3507.
10. Hojo, M.; Murakami, C.; Fujii, A.; Hosomi, A. Tetrahedron Lett. 1999, 40, 911.
11. 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.
12. 4b