Enantioselective Preparation of cis-β-Azidocyclopropane Esters by Cyclopropanation of Azido Alkenes Using a Chiral Dirhodium Catalyst

被引：49

作者：

Gu, Peiming ^{[1
,2
,3
]}

Su, Yan ^{[1
,2
,3
]}

Wu, Xiu-Ping ^{[1
,2
]}

Sun, Jian ^{[1
,2
]}

Liu, Wanyi ^{[1
,2
]}

Xue, Ping ^{[1
,2
]}

Li, Rui ^{[1
,2
]}

机构：

[1] Ningxia Univ, Key Lab Energy Sources & Engn, State Key Lab Cultivat Base Nat Gas Convers, Yinchuan 750021, Peoples R China

[2] Ningxia Univ, Dept Chem, Yinchuan 750021, Peoples R China

[3] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 09期

关键词：

AMINOCYCLOPROPANE CARBOXYLIC-ACIDS; ASYMMETRIC CYCLOPROPANATION; RUTHENIUM; PEPTIDES; LIGANDS; RING;

D O I：

10.1021/ol3006437

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A diastereo- and enantiocontrolled preparation of the conformationally restricted cis-beta-azidocyclopropane esters have been developed. The Rh-2(S-DOSP)(4) was found to be an efficient catalyst in hexane for the cyclopropanation of azido alkenes with diazo esters, and 19 cis-beta-azidocyclopropane esters were prepared in excellent yields. The value of the diastereomer ratio was up to 99:1, and the enantiomeric excess was up to 95%. Furthermore, the relative and absolute configuration was confirmed by X-ray analysis.

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页码：2246 / 2249

页数：4

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