醛对硝基乙烯的对映选择性有机催化迈克尔加成反应：高效合成γ2-氨基酸
Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene: efficient access to gamma2-amino acids.
作者信息
Chi Yonggui, Guo Li, Kopf Nathan A, Gellman Samuel H
机构信息
Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, USA.
出版信息
J Am Chem Soc. 2008 Apr 30;130(17):5608-9. doi: 10.1021/ja800345r. Epub 2008 Apr 4.
Abstract
Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene catalyzed by (S)-diphenylprolinol silyl ether provides beta-substituted-delta-nitroalcohols in nearly optically pure form (96-99% ee). The Michael adducts bear a single substituent adjacent to the carbonyl and can be efficiently converted to protected gamma2-amino acids, which are essential for the systematic conformational studies of gamma-peptide foldamers.
摘要
（S）-二苯基脯氨醇硅醚催化醛与硝基乙烯的对映选择性有机催化迈克尔加成反应，可提供几乎光学纯形式（对映体过量96 - 99%）的β-取代-δ-硝基醇。迈克尔加合物在羰基相邻位置带有单个取代基，并且可以有效地转化为受保护的γ2-氨基酸，这对于γ-肽折叠体的系统构象研究至关重要。
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