Facial diastereoselectivity in the [2+2]-photocycloaddition of chiral vinylglycine-derived N,N-diallyl amines

被引：18

作者：

Bach, T ^{[1
]}

Pelkmann, C ^{[1
]}

Harms, K ^{[1
]}

机构：

[1] Univ Marburg, Fachbereich Chem, D-35032 Marburg, Germany

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 11期

关键词：

amino acids and derivatives; asymmetric induction; cycloadditions; photochemistry;

D O I：

10.1016/S0040-4039(99)00158-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The vinylglycine-derived N-cinnamyl-N-allyl carbamates 1, 4 and 7 were prepared and their sensitized intramolecular [2+2]-photocycloaddition to the exo-products 2, 5 and 6 was studied (53-77% yield). Perfect facial diastereoselection (d.r. = >95/5) was observed in the photocycloaddition of the rigid oxazolidinone 4 and of the conformationally fixed acyclic carbamate 7. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2103 / 2104

页数：2