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Ambivalent Reactivity Modes of β‐Chlorovinyl Ketones: Electrophilic Lithium [3]Cumulenolates from Soft Vinyl Enolization Strategy
Author(s) -
Kim Hun Young,
Rooney Edward Oscar,
Meury Raymond Phillip,
Oh Kyungsoo
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201302750
Subject(s) - keto–enol tautomerism , electrophile , lithium (medication) , nucleophile , chemistry , vinyl chloride , reactivity (psychology) , organic chemistry , medicinal chemistry , catalysis , psychiatry , psychology , medicine , polymer , alternative medicine , pathology , copolymer
Soft spot : The soft vinyl enolization of ( E )‐β‐chlorovinyl ketones results in the in situ generation of electrophilic lithium [3]cumulenolates, which react with nucleophiles such as another lithium [3]cumulenolate to stereoselectively form vinyl allenones. They can also react with ketimine esters to give 3‐methylenepyrrolidines.