Chiral aminocyclopentene-based cycloaddition strategies to bicyclic [3.3.0] rings

被引：10

作者：

Cai, Chaozhong ^{[1
]}

Kang, Fu-An ^{[1
]}

Beauchamp, Derek A. ^{[2
]}

Sui, Zhihua ^{[1
]}

Russell, Ronald K. ^{[2
]}

Teleha, Christopher A. ^{[2
]}

机构：

[1] Janssen Pharmaceut Res & Dev, Metab Dis Res, Spring House, PA 19477 USA

[2] Janssen Pharmaceut Res & Dev, High Output Synth Team HOPS, CREATe, Spring House, PA 19477 USA

来源：

TETRAHEDRON-ASYMMETRY | 2013年 / 24卷 / 11期

关键词：

D O I：

10.1016/j.tetasy.2013.04.014

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Two cycloaddition methods were applied to chiral protected aminocyclopentenes 2 and 9 and provided novel bicyclic products 3 and 4 in good yields. The explanation for the observed stereochemistry was based on the sterically encumbered beta-face forcing the cycloadditions to occur on the alpha-face of the cyclopentene ring. The stereochemistry of 4 was confirmed by X-ray of the fumarate salt 10 and showed the trans-relationship between the newly formed ring and the chiral -NHBoc group. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：651 / 656

页数：6

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