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Formal Asymmetric (4+1) Annulation Reaction between Sulfur Ylides and 1,3‐Dienes
Author(s) -
Rousseau Olivier,
Delaunay Thierry,
Dequirez Geoffroy,
TrieuVan Tran,
Robeyns Koen,
Robiette Raphaël
Publication year - 2015
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.201502579
Subject(s) - cyclopropanation , annulation , enantioselective synthesis , stereospecificity , stereoselectivity , sulfur , chemistry , stereochemistry , combinatorial chemistry , organic chemistry , catalysis
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 MgI 2 ‐catalyzed rearrangement of vinylcyclopropanes. This method is distinguished by a remarkable compatibility with functional groups and a high stereocontrol.