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Literature DB >> 15547995

Lewis acid-mediated selective chlorinations of silyl enolate.

Yanhua Zhang¹, Kazutaka Shibatomi, Hisashi Yamamoto.

Abstract

A new method involving efficient, widely applicable, and highly selective alpha-chlorination of simple silyl enolate with Lewis acid and an alpha,alpha-dichloro-1,3-dicarbonyl controller unit was reported. Diastereoselectivity and enantioselectivity of the reaction were investigated. High reactivity and selectivity were achieved by using alpha,alpha-dichlorinated malonic ester.

Entities: Chemical

Year: 2004 PMID： 15547995 DOI： 10.1021/ja0454485

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

9 in total

1. Alpha-olefins as alkenylmetal equivalents in catalytic conjugate addition reactions.

Authors: Chun-Yu Ho; Hirohisa Ohmiya; Timothy F Jamison
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

2. Stereoselective synthesis of alpha,alpha-chlorofluoro carbonyl compounds leading to the construction of fluorinated chiral quaternary carbon centers.

Authors: Kazutaka Shibatomi; Hisashi Yamamoto
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

Lewis acid-mediated selective chlorinations of silyl enolate.

1. Alpha-olefins as alkenylmetal equivalents in catalytic conjugate addition reactions.

2. Stereoselective synthesis of alpha,alpha-chlorofluoro carbonyl compounds leading to the construction of fluorinated chiral quaternary carbon centers.

3. Chiral calcium VAPOL phosphate mediated asymmetric chlorination and Michael reactions of 3-substituted oxindoles.

4. Achiral counterion control of enantioselectivity in a Brønsted acid-catalyzed iodolactonization.

5. Catalytic Addition of Simple Alkenes to Carbonyl Compounds Using Group 10 Metals.

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8. Enantioselective synthesis of tertiary α-chloro esters by non-covalent catalysis.

9. Enantioselective decarboxylative chlorination of β-ketocarboxylic acids.