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Ferric Chloride Hexahydrate‐Catalyzed Highly Regio‐ and Stereoselective Conjugate Addition Reaction of 2,3‐Allenoates with Grignard Reagents: An Efficient Synthesis of β,γ‐Alkenoates
Author(s) -
Chai Guobi,
Lu Zhan,
Fu Chunling,
Ma Shengming
Publication year - 2009
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.200900091
Subject(s) - chemistry , stereoselectivity , allylic rearrangement , catalysis , ferric , electrophile , reagent , medicinal chemistry , magnesium , regioselectivity , aryl , chloride , alkyl , organic chemistry
Abstract Ferric chloride hexahydrate was shown to be an efficient catalyst for the conjugate addition of 2,3‐allenoates with alkyl‐, aryl‐, or vinyl‐Grignard reagents to synthesize polysubstituted β,γ‐unsaturated alkenoates with high regio‐ and stereoselectivity. The in situ formed magnesium dienolate may readily react with different electrophilic reagents under different reaction conditions with or without a catalyst to construct an allylic quaternary carbon at the α‐position of the ester group and a stereocontrollable retention of the carbon‐carbon double bond.