Stereoselective Synthesis of Cyclobutanes by Contraction of Pyrrolidines | Zendy

Chunngai Hui | Zendy; Lukas Brieger | Zendy; Carsten Strohmann | Zendy; Andrey P. Antonchick | Zendy

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Stereoselective Synthesis of Cyclobutanes by Contraction of Pyrrolidines

Author(s) -

Chunngai Hui,

Lukas Brieger,

Carsten Strohmann,

Andrey P. Antonchick

Publication year - 2021

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.1c10175

Subject(s) - cyclobutanes , chemistry , stereospecificity , stereocenter , stereoselectivity , natural product , stereochemistry , combinatorial chemistry , organic chemistry , enantioselective synthesis , cycloaddition , catalysis

Here we report a contractive synthesis of multisubstituted cyclobutanes containing multiple stereocenters from readily accessible pyrrolidines using iodonitrene chemistry. Mediated by a nitrogen extrusion process, the stereospecific synthesis of cyclobutanes involves a radical pathway. Unprecedented unsymmetrical spirocyclobutanes were prepared successfully, and a concise, formal synthesis of the cytotoxic natural product piperarborenine B is reported.

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