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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.