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Enolic Ortho Esters. III. Preparation of a Keto Acetal by Hydride Reduction of an Enolic Ortho Ester

โœ Scribed by Collins, DJ; Downes, LM; Kyriakou, M


Book ID
121077601
Publisher
Commonwealth Scientific and Industrial Research Organisation Publishing
Year
1989
Tongue
English
Weight
250 KB
Volume
42
Category
Article
ISSN
0004-9425

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Reaction of the enolic ortho ester (1) with the ketene silyl acetals (2a-c) in dichloromethane in the presence of titanium tetrachloride at low temperatures gave the respective keto acetal esters (6a-c) via the titanium enolates (3a-c).

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The mrcrobral reduchon of l'-ethylpropyl 2-methyl-3-oxopentanoate, a j3-keto ester possessmg bulky subsutuent, as well as the cormspondmg enol ester was exammed Eprmenc nuxture of hydroxy ester, contammg (2S.3.Qisomer as the major product (9296e e ,43%d e ) was obtamed via the reducuon of enol ester