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

Xinxin Shao | Zendy; Steven J. Malcolmson | Zendy

Open Access

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

Author(s) -

Xinxin Shao,

Steven J. Malcolmson

Publication year - 2019

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.9b02692

Subject(s) - stereocenter , cyclopropanation , chemistry , quaternary carbon , quaternary , catalysis , carbon fibers , bearing (navigation) , stereochemistry , combinatorial chemistry , enantioselective synthesis , organic chemistry , paleontology , geography , computer science , geology , composite number , cartography , algorithm

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 α-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.

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