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Formal Asymmetric (4+1) Annulation Reaction between Sulfur Ylides and 1,3-Dienes.

Authors :
Rousseau O
Delaunay T
Dequirez G
Trieu-Van T
Robeyns K
Robiette R
Source :
Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2015 Sep 07; Vol. 21 (37), pp. 12899-902. Date of Electronic Publication: 2015 Jul 31.
Publication Year :
2015

Abstract

A highly enantioselective synthesis of functionalized cyclopentanoids by a formal asymmetric (4+1) annulation strategy was developed. The methodology consists of a stereoselective cyclopropanation reaction between chiral sulfur ylides and 1,3-dienes followed by a, in situ, stereospecific MgI2 -catalyzed rearrangement of vinylcyclopropanes. This method is distinguished by a remarkable compatibility with functional groups and a high stereocontrol.<br /> (© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Details

Language :
English
ISSN :
1521-3765
Volume :
21
Issue :
37
Database :
MEDLINE
Journal :
Chemistry (Weinheim an der Bergstrasse, Germany)
Publication Type :
Academic Journal
Accession number :
26235566
Full Text :
https://doi.org/10.1002/chem.201502579