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

页码：7380 / 7385

页数：6

共 45 条

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Fu, Peng
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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (16) : 5530 - 5541
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Wang, Zehua
Zhu, Yasheng
Pan, Xiaoguang
Wang, Gang
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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (08) : 3053 - 3057
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Ashimori, A
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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (26) : 6477 - 6487
[45] Catalytic asymmetric synthesis of quaternary carbon centers.: Exploratory investigations of intramolecular Heck reactions of (E)-α,β-unsaturated 2-haloanilides and analogs to form enantioenriched spirocyclic products.
Ashimori, A
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Poon, DJ
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (01) : 192 - 192

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