Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 10, Pages 3942-3945Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo702318d
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A novel stereoselective synthetic approach to (Z)-trifluoromethylalkene dipeptide isosteres (CF(3)-ADIs) is described. Starting from readily available N-BOC-L-phenylalanine, Phe-Gly type CF(3)-ADIs were obtained through palladium-catalyzed carbonylation of allylic carbonates under CO. While the reaction of N-Boc derivatives proceeds in excellent yields but lower stereoselectivity (E:Z = 62:38-43:57), the reaction of the NN-diBoc derivative exclusively affords the desired (Z)-isomer in 61% yield. We also present a highly stereoselective synthesis of several Phe-Gly type trisubstituted alkene dipeptide isosteres by palladium-catalyzed carbonylation.
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