Catalytic, Asymmetric α-Fluorination of Acid Chlorides: Dual Metal−Ketene Enolate Activation
نویسندگان
چکیده
منابع مشابه
Catalytic, asymmetric alpha-fluorination of acid chlorides: dual metal-ketene enolate activation.
In this Communication, we disclose a catalytic, highly enantioselective (up to >99% ee) alpha-fluorination of acid chlorides to produce a variety of optically active carboxylic acid derivatives from readily accessible and commercially available starting materials. The reaction depends on dually activated ketene enolates generated from two discrete catalysts--a chiral nucleophile and an achiral ...
متن کاملTricomponent catalytic α,α-difluorination of acid chlorides.
The selective α,α-difluorination of carbonyl compounds remains a challenge in modern organic synthesis; current methods often incorporate stepwise processes and/or harsh conditions, providing unsatisfactory mixtures of mono- and difluorinated products. In this communication, a practical, mild, and one-pot method for the selective α,α-difluorination of readily available acid chlorides is reporte...
متن کاملFrom bifunctional to trifunctional (tricomponent nucleophile-transition metal-lewis acid) catalysis: the catalytic, enantioselective α-fluorination of acid chlorides.
We report in full detail our studies on the catalytic, asymmetric α-fluorination of acid chlorides, a practical method that produces an array of α-fluorocarboxylic acid derivatives in which improved yield and virtually complete enantioselectivity are controlled through electrophilic fluorination of a ketene enolate intermediate. We discovered, for the first time, that a third catalyst, a Lewis ...
متن کاملOrganocatalytic asymmetric fluorination of α-chloroaldehydes involving kinetic resolution
In a previous study it was shown that the enantioselective α-fluorination of racemic α-chloroaldehydes with a chiral organocatalyst yielded the corresponding α-chloro-α-fluoroaldehydes with high enantioselectivity. It was also revealed that kinetic resolution of the starting aldehydes was involved in this asymmetric fluorination. This paper describes the determination of the absolute stereochem...
متن کاملScalable methodology for the catalytic, asymmetric alpha-bromination of acid chlorides.
The optimization of a practical, catalytic, asymmetric process for the alpha-bromination of acid chlorides to produce synthetically versatile, optically active alpha-bromoesters is reported. A range of products is produced in high enantioselectivity and moderate to good chemical yields with retention of both upon scale-up. The reactions herein are catalyzed by cinchona alkaloid derivatives, wit...
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ژورنال
عنوان ژورنال: Journal of the American Chemical Society
سال: 2008
ISSN: 0002-7863,1520-5126
DOI: 10.1021/ja807792c