Diastereoselective [3+2]-photocycloaddition of chiral 1,4-naphthalenedicarboxylic esters to alkenes

被引：11

作者：

Kubo, Y ^{[1
]}

Yoshioka, M ^{[1
]}

Nakajima, S ^{[1
]}

Inamura, I ^{[1
]}

机构：

[1] Shimane Univ, Fac Sci & Engn, Dept Mat Sci, Matsue, Shimane 6908504, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 12期

关键词：

photochemistry; diastereoselection; cycloadditions; esters;

D O I：

10.1016/S0040-4039(99)00180-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[3+2]-Photocycloaddition of di-(-)-menthyl, di-(-)-8-phenylmenthyl, and di-(-)-bornyl 1,4-naphthalenedicarboxylates to alkenes, such as isobutene, styrene, and alpha-methylstyrene, proceeded with diastereoselectivity, up to 62% diastereomeric excess (de), largely depending on the concavity of the auxiliary, steric bulk of the substituents of the alkenes, and reaction temperature. The de values remarkably increased with decrease of the reaction temperature, and linear dependence of In(diastereomeric ratio) on 1/T was observed. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2335 / 2338

页数：4

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