相转移催化不对称烷基化 α-苯甲酰氧基-β-酮酯：拥挤的 2,3-二羟基羧酸酯的立体选择性构建。

Phase-transfer-catalyzed asymmetric alkylation of alpha-benzoyloxy-beta-keto esters: stereoselective construction of congested 2,3-dihydroxycarboxylic acid esters.

机构信息

Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto, 606-8502, Japan.

出版信息

Chem Asian J. 2010 Mar 1;5(3):562-70. doi: 10.1002/asia.200900344.

DOI:10.1002/asia.200900344

Abstract

Highly enantioselective phase-transfer-catalyzed alkylation of tert-butyl 2-benzoyloxy-3-oxobutanoate was realized by the use of an N-spiro chiral quaternary ammonium salt, as a complementary approach to the asymmetric hydroxylation of alpha-alkyl-beta-keto esters. The synthetic utility of the alkylated compounds is highlighted by the diastereoselective reduction and alkylation of the remaining ketone moiety to give various enantiomerically enriched congested 2,3-dihydroxycarboxylic acid esters.

摘要

通过使用 N-螺环手性季铵盐，实现了叔丁基 2-苯甲酰氧基-3-氧代丁酸酯的高对映选择性相转移催化烷基化，这是对α-烷基-β-酮酯不对称羟化的补充方法。通过剩余酮部分的非对映选择性还原和烷基化，所得到的烷基化化合物具有很高的合成实用性，可得到各种对映体富集的稠合 2,3-二羟基羧酸酯。

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