Control of the mode selectivity (ene reaction versus [2+2] cycloaddition) in the photooxygenation of ene carbamates: Directing effect of an alkenylic nitrogen functionality

被引：32

作者：

Adam, W

Bosio, SG

Turro, NJ

机构：

[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

[2] Columbia Univ, Dept Chem, New York, NY 10027 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 47期

关键词：

D O I：

10.1021/ja028407m

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The geometry of the double bond in oxazolidinone-substituted ene carbamates controls the mode selectivity (ene reaction versus [2+2] cycloaddition) of singlet oxygen through stereoelectronic effects, whereas the chiral auxiliary provides high diastereoselectivity through steric shielding. Copyright © 2002 American Chemical Society.

引用

页码：14004 / 14005

页数：2

共 16 条

[11] MECHANISM OF THE ENE REACTION OF SINGLET OXYGEN WITH OLEFINS
HARDING, LB
GODDARD, WA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (02) : 439 - 449
[12] SELECTION OF O2(1DELTAG) - OLEFIN REACTION COURSES - INTERMOLECULAR NONBONDED ATTRACTION AND PI-BOND POLARITY OF OLEFINS
INAGAKI, S
FUJIMOTO, H
FUKUI, K
[J]. CHEMISTRY LETTERS, 1976, (07) : 749 - 752
[13] LERDAL D, 1978, TETRAHEDRON LETT, P3227
[14] Singlet oxygenation of 1-aminomethyl-1-tert-butyl-2-methoxy-2-(3-methoxy-phenyl)ethylenes: Marked effect of allylic nitrogen on the reaction pathways and chemoselectivity
Matsumoto, M
Kitano, Y
Kobayashi, H
Ikawa, H
[J]. TETRAHEDRON LETTERS, 1996, 37 (45) : 8191 - 8194
[15] Effect of allylic oxygen on the reaction pathways of singlet oxygenation: Selective formation of 1,2-dioxetanes from 1-alkoxymethyl-2-aryl-1-tert-butyl-2-methoxyethylenes
Matsumoto, M
Kobayashi, H
Matsubara, J
Watanabe, N
Yamashita, S
Oguma, D
Kitano, Y
Ikawa, H
[J]. TETRAHEDRON LETTERS, 1996, 37 (03) : 397 - 400
[16] ROUSSEAU G, 1977, TETRAHEDRON LETT, P2517

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