Sequential Wittig Olefination–Catalytic Asymmetric Epoxidation with Reuse of Waste Ph 3 P(O): Application of α,β‐Unsaturated  N ‐Acyl Pyrroles as Ester Surrogates | Zendy

Kinoshita Tomofumi | Zendy; Okada Shigemitsu | Zendy; Park SunRyung | Zendy; Matsunaga Shigeki | Zendy; Shibasaki Masakatsu | Zendy

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Sequential Wittig Olefination–Catalytic Asymmetric Epoxidation with Reuse of Waste Ph 3 P(O): Application of α,β‐Unsaturated N ‐Acyl Pyrroles as Ester Surrogates

Author(s) -

Kinoshita Tomofumi,

Okada Shigemitsu,

Park SunRyung,

Matsunaga Shigeki,

Shibasaki Masakatsu

Publication year - 2003

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200352509

Subject(s) - wittig reaction , chemistry , catalysis , samarium , pyrrole , organic chemistry , selectivity , reactivity (psychology) , conjugated system , medicine , polymer , alternative medicine , pathology

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 Ph 3 P(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.

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