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Highly Diastereo- and Enantioselective Vinylogous Mannich Reactions of Fluorinated Aldimines with Siloxyfurans

✍ Scribed by Qian-Yi Zhao; Zhi-Liang Yuan; Min Shi

Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
230 KB
Volume
353
Category
Article
ISSN
1615-4150

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✦ Synopsis

Abstract

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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