Catalytic Enantio- and Diastereoselective Cyclopropanation of 2-Azadienes for the Synthesis of Aminocyclopropanes Bearing Quaternary Carbon Stereogenic Centers

被引：21
|
作者：
Shao, Xinxin [1 ]
Malcolmson, Steven J. [1 ]
机构：
[1] Duke Univ, Dept Chem, Durham, NC 27708 USA
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 18期
关键词：
HIGHLY ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC CYCLOPROPANATION; 3+2 ANNULATION; RHODIUM; DERIVATIVES; 3-SPIROCYCLOPROPYL-2-OXINDOLES; VINYLDIAZOACETATES; CYCLOPROPENES; NUCLEOSIDES; PEPTIDES;
D O I：
10.1021/acs.orglett.9b02692
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report the catalytic enantio-and diastereoselective preparation of aminocyclopropanes by the cyclopropanation of terminal and (Z)-internal 2-azadienes with donor/acceptor carbenes derived from alpha-diazoesters. The resulting cyclopropanes bear quaternary carbon stereogenic centers vicinal to the amino-substituted carbon and are formed as a single diastereomer in up to 99:1 er and 97% yield with 0.5 mol % of Rh-2(DOSP)(4) and only 1.5 equiv of the diazo reagent. Transformations with internal azadienes afford cyclopropanes with three contiguous stereogenic centers.
引用
收藏
页码：7380 / 7385
页数：6
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