Journal
ORGANIC LETTERS
Volume 13, Issue 9, Pages 2426-2429Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol200649u
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Funding
- National Institute of General Medical Sciences [R01 GM084927]
- Novartis
- Amgen
- BMS
- NIH NRSA
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A simple and efficient method for the preparation of beta-stereogenic alpha-keto esters is described using a copper(II)-catalyzed aerobic deacylation of substituted acetoacetate esters. The substrates for the title process arise from catalytic, enantioselective conjugate additions and alkylation reactions of acetoacetate esters. The mild conditions do not induce racemization of the incipient enolizable alpha-keto ester. The reaction is tolerant of esters, certain ketones, ketals, and nitro groups and utilizes inexpensive, readily available materials.
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