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.
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页码：1957 / 1963
页数：7
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