Sequential Wittig Olefination-Catalytic Asymmetric Epoxidation with Reuse of Waste Ph3P(O): Application of α,β-Unsaturated N-Acyl Pyrroles as Ester Surrogates

Waste not, want not: Efficient one‐pot access to optically active epoxides with 96 to 99.5 % ee from a variety of aldehydes is described. In a sequential process, the Ph3P(O) by‐product of a Wittig reaction acts as a modulator for the samarium catalyst in the asymmetric epoxidation of the conjugated...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2003-10, Vol.42 (38), p.4680-4684
Main Authors: Kinoshita, Tomofumi, Okada, Shigemitsu, Park, Sun-Ryung, Matsunaga, Shigeki, Shibasaki, Masakatsu
Format: Article
Language:English
Subjects:
asymmetric catalysis
epoxidation
samarium
synthetic methods
Wittig reactions
Online Access:Get full text
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Summary:Waste not, want not: Efficient one‐pot access to optically active epoxides with 96 to 99.5 % ee from a variety of aldehydes is described. In a sequential process, the Ph3P(O) by‐product of a Wittig reaction acts as a modulator for the samarium catalyst in the asymmetric epoxidation of the conjugated N‐acyl pyrrole Wittig product (see scheme). The N‐acyl pyrrole functionality is key to the high reactivity and selectivity observed. R=alkyl, aryl, vinyl.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200352509