One-Step Synthesis of 1‑Chloro-3-arylacetone Derivatives from Arylacetic Acids

A practical one-step method has been developed to prepare α-chloroketones from readily available, inexpensive phenylacetic acid derivatives. The method utilizes the unique reactivity of an intermediate Mg–enolate dianion, which displays selectivity for the carbonyl carbon of chloromethyl carbonyl el...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 79; no. 18; pp. 8917 - 8925
Main Authors Zacuto, Michael J, Dunn, Robert F, Figus, Margaret
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.09.2014
Amer Chemical Soc
Subjects
Acetone - analogs & derivatives
Acetone - chemical synthesis
Acetone - chemistry
Biological Products - chemical synthesis
Biological Products - chemistry
Catalysis
Chemistry
Chemistry, Organic
Phenylacetates - chemistry
Phenylpropionates - chemical synthesis
Phenylpropionates - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
KETONES
ROUTE
ASYMMETRIC-SYNTHESIS
ALPHA-CHLOROKETONES
CIMIRACEMATE-B
BLACK COHOSH
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Summary:A practical one-step method has been developed to prepare α-chloroketones from readily available, inexpensive phenylacetic acid derivatives. The method utilizes the unique reactivity of an intermediate Mg–enolate dianion, which displays selectivity for the carbonyl carbon of chloromethyl carbonyl electrophiles. Decarboxylation of the intermediate occurs spontaneously during the reaction quench. The utility of the reaction products has been demonstrated through the total synthesis of the natural product cimiracemate B.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo5016486