Journal
ORGANIC LETTERS
Volume 10, Issue 19, Pages 4375-4378Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol8018456
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Funding
- National Institutes of General Medical Sciences
- DHHS [GM066153]
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An efficient synthesis of high enantiopurity N-protected alpha-amino ketones is described. Complementing other studies using boronic acids and thiol esters, this Cu(I) diphenylphosphinate (CuDPP)-mediated, palladium-catalyzed coupling of alpha-amino thiol esters with aryl, heteroaryl, allyl, and alkenyl organostannanes gives N-protected alpha-amino ketones in high yields with high enantiopurity (in almost all cases) under mild and pH-neutral reaction conditions. The viability of pi-deficient heteroarylstannanes is an advantage of this reaction compared to the related boronic acid system.
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