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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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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