CONJUGATE ADDITION OF CHLORIDE TO ALPHA,BETA-UNSATURATED CHIRAL IMIDES PROMOTED BY BCL3-DERIVATIVES .2.

被引：12

作者：

CARDILLO, G

DIMARTINO, E

GENTILUCCI, L

TOMASINI, C

TOMASONI, L

机构：

[1] Centro per lo Studio della Fisica delle Macromolecole, Dipartimento di Chimica G. Ciamician Università di Bologna, 40126 Bologna, Via Selmi

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 08期

关键词：

D O I：

10.1016/0957-4166(95)00255-N

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The diastereoselective hydrochlorination of alpha,beta-unsaturated chiral imides by reaction with BCl(2)OR or BCl(OR)(2) type reagents is described. Complete diastereoselectivity is achieved through the use of new oxazolidin-2-ones ad hoc prepared for this purpose from (S)-tryptophan. An hypothesis on the donor-acceptor interactions, between the substrate and the Lewis acids, that drive the attack of the chloride preferentially to one face of the alkenoyl chain is reported.

引用

页码：1957 / 1963

页数：7

共 15 条

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