Ring‐Opening Regio‐, Diastereo‐, and Enantioselective 1,3‐Chlorochalcogenation of Cyclopropyl Carbaldehydes | Zendy

Wallbaum Jan | Zendy; Garve Lennart K. B. | Zendy; Jones Peter G. | Zendy; Werz Daniel B. | Zendy

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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 , enamine , ring (chemistry) , iminium , stereochemistry , 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).

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