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Ring‐Opening Regio‐, Diastereo‐, and Enantioselective 1,3‐Chlorochalcogenation of Cyclopropyl Carbaldehydes
Author(s) -
Wallbaum Jan,
Garve Lennart K. B.,
Jones Peter G.,
Werz Daniel B.
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201605265
Subject(s) - enantioselective synthesis , stereocenter , desymmetrization , regioselectivity , chemistry , iminium , enamine , stereochemistry , ring (chemistry) , medicinal chemistry , organic chemistry , catalysis
meso ‐Cyclopropyl carbaldehydes are treated in the presence of an organocatalyst with sulfenyl and selenyl chlorides to afford 1,3‐chlorochalcogenated products. The transformation is achieved by a merged iminium–enamine activation. The enantioselective desymmetrization reaction, leading to three adjacent stereocenters, furnished the target products in complete regioselectivity and moderate to high diastereo‐ and enantioselectivities (d.r. up to 15:1 and e.r. up to 93:7).