Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Nagoya 464-8603, Japan.
J Am Chem Soc. 2012 Apr 25;134(16):6972-5. doi: 10.1021/ja3022939. Epub 2012 Apr 12.
A new strategy for developing stereoselective bond-forming reactions is introduced; it takes advantage of the ionic nucleophilic catalysis of chiral ammonium betaines to utilize vinylic esters simultaneously as the enolate precursor and the acylating agent for coupling with electrophiles. Its synthetic utility is clearly demonstrated by the realization of a highly diastereo- and enantioselective aldol reaction from oxindole-derived vinylic carbonates.
介绍了一种开发立体选择性成键反应的新策略；它利用手性季铵盐的离子亲核催化作用，使乙烯基酯同时作为烯醇化物前体和酰化剂，与亲电试剂进行偶联。通过实现吲哚衍生的乙烯基碳酸酯的高非对映选择性和对映选择性Aldol 反应，清楚地证明了其合成实用性。
