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Highly Diastereo‐ and Enantioselective Vinylogous Mannich Reactions of Fluorinated Aldimines with Siloxyfurans
Author(s) -
Zhao QianYi,
Yuan ZhiLiang,
Shi Min
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000843
Subject(s) - enantioselective synthesis , chemistry , aldimine , oxazoline , organic chemistry , enantiomer , mannich reaction , stereochemistry , medicinal chemistry , catalysis
A highly regio‐ and enantioselective asymmetric vinylogous Mannich reaction of readily available fluorinated aldimines bearing a chiral auxiliary [( S )‐1‐phenylethyl group] with siloxyfurans to afford chiral fluorine‐containing γ‐butenolide or γ‐lactone derivatives has been developed in the presence of silver acetate (10 mol%) and axially chiral phosphine‐oxazoline ligand L1 (11 mol%). In most cases, the corresponding fluorinated adducts were obtained in high yields, good to excellent enantiomeric excesses and up to>20:1 dr .
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