Formal Asymmetric (4+1) Annulation Reaction between Sulfur Ylides and 1,3‐Dienes | Zendy

Rousseau Olivier | Zendy; Delaunay Thierry | Zendy; Dequirez Geoffroy | Zendy; TrieuVan Tran | Zendy; Robeyns Koen | Zendy; Robiette Raphaël | Zendy

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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.

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