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

Xinxin Shao and Steven J. Malcolmson*

*Department of Chemistry, Duke University, Durham, North Carolina 27708, United States, Email: steven.malcolmsonduke.edu

X. Shao, S. J. Malcolmson, Org. Lett., 2019, 21, 7380-7385.

DOI: 10.1021/acs.orglett.9b02692 (free Supporting Information)


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Abstract

A Rh-catalyzed enantio- and diastereoselective cyclopropanation of terminal and (Z)-internal 2-azadienes with donor/acceptor carbenes derived from α-diazoesters provides aminocyclopropanes with quaternary carbon stereogenic centers vicinal to the amino-substituted carbon. Transformations with internal azadienes afford cyclopropanes with three contiguous stereogenic centers.

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Key Words

cyclopropanes


ID: J54-Y2019