Ambivalent Reactivity Modes of β‐Chlorovinyl Ketones: Electrophilic Lithium [3]Cumulenolates from Soft Vinyl Enolization Strategy | Zendy

Kim Hun Young | Zendy; Rooney Edward Oscar | Zendy; Meury Raymond Phillip | Zendy; Oh Kyungsoo | Zendy

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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.

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