Chiral aminoalcohols with a menthane skeleton as catalysts for the enantioselective addition of diethylzinc to benzaldehyde

被引：49
作者：
Panev, S
Linden, A
Dimitrov, V [1 ]
机构：
[1] Bulgarian Acad Sci, Inst Organ Chem, BU-1113 Sofia, Bulgaria
[2] Univ Zurich, Inst Organ Chem, CH-8057 Zurich, Switzerland
来源：
TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 09期
关键词：
D O I：
10.1016/S0957-4166(01)00206-3
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Novel chiral aminoalcohols were synthesized by highly diastereoselective addition of Me3SiCN and LICH2CN to (-)-menthone followed by LiAlH4 reduction. The addition of CH2=CH-MgBr and PhCH=CH-MgBr to menthone and the following epoxidation, provided useful hydroxy epoxides, one of which could be aminolyzed to afford an aminodiol. In one case, the configuration of the newly formed epoxidic stereogenic center was determined by X-ray crystallography. When applied as catalysts in the enantioselective addition of Et2Zn to benzaldehyde, the aminoalcohols induced enantiomeric excesses (e.e.s) of up to 77%. (C) 2001 Elsevier Science Ltd. All rights reserved.
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页码：1313 / 1321
页数：9
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