Ambivalent Reactivity Modes of β‐Chlorovinyl Ketones: Electrophilic Lithium [3]Cumulenolates from Soft Vinyl Enolization Strategy1. Issue 31 (20th June 2013)

• Record Type: Journal Article
• Authors: Kim, Hun Young; Rooney, Edward Oscar; Meury, Raymond Phillip; Oh, Kyungsoo
• Is Part Of: Angewandte Chemie international edition. Volume 52:Issue 31(2013)
• Page Start: 8026
• Page End: 8030
• Publication Date: 2013-06-20
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201302750
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="graphical" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p> <bold>Soft spot</bold>: The soft vinyl enolization of (<italic>E</italic>)‐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.<boxed-text content-type="graphic" position="anchor" orientation="portrait"><graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg276x431z" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></boxed-text></p> </abstract>