Stereoselective Simmons–Smith Cyclopropanation of Chiral Enamides | Zendy

Song Zhenlei | Zendy; Lu Ting | Zendy; Hsung Richard P. | Zendy; AlRashid Ziyad F. | Zendy; Ko Changhong | Zendy; Tang Yu | Zendy

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Stereoselective Simmons–Smith Cyclopropanation of Chiral Enamides

Author(s) -

Song Zhenlei,

Lu Ting,

Hsung Richard P.,

AlRashid Ziyad F.,

Ko Changhong,

Tang Yu

Publication year - 2007

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200700681

Subject(s) - cyclopropanation , stereoselectivity , combinatorial chemistry , chemistry , stereochemistry , organic chemistry , catalysis

Efficient and practical access to chiral aminocyclopropanes is secured by the title reaction (see example). Both E and Z enamides undergo the cyclopropanation with high diastereoselectivity (d.r. up to >95:5). The application of this methodology to the synthesis of biologically significant aminocyclopropanes illustrates the potential of chiral enamides as useful building blocks for stereoselective organic synthesis.

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