Volume 42, Issue 21
Preparative Organic Chemistry

ChemInform Abstract: Nucleophilic α-Arylation and α-Alkylation of Ketones by Polarity Inversion of N-Alkoxyenamines: Entry to the Umpolung Reaction at the α-Carbon Position of Carbonyl Compounds.

Tetsuya Miyoshi

Tetsuya Miyoshi

Kobe Pharm. Univ., Higashinada, Kobe 658, Japan

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Takayuki Miyakawa

Takayuki Miyakawa

Kobe Pharm. Univ., Higashinada, Kobe 658, Japan

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Masafumi Ueda

Masafumi Ueda

Kobe Pharm. Univ., Higashinada, Kobe 658, Japan

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Okiko Miyata

Okiko Miyata

Kobe Pharm. Univ., Higashinada, Kobe 658, Japan

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First published: 28 April 2011

Abstract

The efficient and transition metal free umpolung reaction by polarity inversion at the β-position of N-alkoxyenamines is characterized by mild conditions and simple transformation of ketones such as (I) into α-substituted ketones (IV) without isolation of the intermediate enamine derivatives (II).

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