Highly diastereoselective synthesis of bicyclo[4.2.0]octanone derivatives by the [2+2] photocycloaddition of chiral cyclohexenonecarboxylates to ethylene

被引：14

作者：

Furutani, A ^{[1
]}

Tsutsumi, K ^{[1
]}

Nakano, H ^{[1
]}

Morimoto, T ^{[1
]}

Kakiuchi, K ^{[1
]}

机构：

[1] Nara Inst Sci & Technol, Grad Sch Mat Sci, Nara 6300192, Japan

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 41期

关键词：

2+2] photocycloaddition; cyclohexenone; chiral auxiliary; menthyl; Lewis acid; diastereoselectivity;

D O I：

10.1016/j.tetlet.2004.08.102

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The diastereoselective [2+2] photocycloaddition of a cyclohexenonecarboxylate containing (-)-8-(4-nitrophenyl)rnentbyI as a chiral auxiliary to ethylene gave the photocycloadduct, a bicyclo[4.2.0]octanone derivative, with a high degree of diastereoselectivity. A photoreaction, conducted in CH2Cl2, at -78degreesC gave the corresponding photocycloadduct in 88% de. In the presence of Ti(OR)(4) or Me3SnCl, the diastereoselectivity was increased up to 92% de. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：7621 / 7624

页数：4

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