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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收藏
页码：2246 / 2249
页数：4
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