Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
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1,4-Addition Reaction of 5H-Oxazol-4-ones to Allenic Esters and Ketones Catalyzed by Chiral Guanidines
Nari JinTomonori MisakiTakashi Sugimura
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JOURNALS OPEN ACCESS

2013 Volume 42 Issue 8 Pages 894-896

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Abstract

In this paper, a chiral guanidine-catalyzed 1,4-addition reaction of 5H-oxazol-4-ones to allenic esters and ketones is described. 5H-Oxazol-4-ones substituted with a 2-chlorophenyl group were suitable pronucleophiles that gave high enantioselectivities. Subsequent hydrolysis of the obtained adduct gave the corresponding γ-butenolide ester without loss of enantiopurity and was transformed into (+)-crobarbatic acid in a few steps.

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© 2013 The Chemical Society of Japan
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