Enantio- and diastereoselective synthesis of highly substituted acylcyclopropanes from homoaldol products by stereospecific homoallylic cyclization

被引：3
|
作者：
Kalkofen, R [1 ]
Brandau, S [1 ]
Ünaldi, S [1 ]
Fröhlich, R [1 ]
Hoppe, D [1 ]
机构：
[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 21期
关键词：
carbocycles; cyclization; small ring systems; asymmetric synthesis; carbonylcyclopropanes;
D O I：
10.1002/ejoc.200500283
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Highly enantioenriched 4-hydroxy-1-alkenyl N,N-diisopropylcarbamates, easily available by asymmetric homoaldol reaction, cyclize by treatment with sodium hydride to form (1r,2t,3t)-configured 1-acylcyclopropanes with high diastereoselectivity. The decisive steps are the migration of the N,N-diisopropylcarbamoyl group onto the alkoxide oxygen atom, followed by an intramolecular homoallylic substitution reaction of the intermediate gamma-carbamoyloxy enolate with inversion of the configuration at the gamma-C atom. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).
引用
收藏
页码：4571 / 4580
页数：10
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