Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 13, Issue 30, Pages 8530-8542Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200700393
Keywords
density functional; calculations; diastereoselectivity fluorine chemistry; Michael reaction; peptides
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Aza-Michael additions of alpha-amino esters to fluorinated acceptors take place in a highly stereoselective manner, to give partially modified Psi-[NHCH2]retropeptides incorporating a hydrolytically stable trifluoroalanine mimic. The reaction mechanism has been investigated experimentally and theoretically, in order to explain the effect of the trifluoromethyl group on the reactivity and the origins of the experimentally observed stereocontrol. The reaction is a two-step process, involving a tandem aza-Michael addition followed by a stereoselective hydrogen transfer. Both steps are base-catalyzed. The high level of stereocontrol is the result of a combination of electrostatic interactions and steric effects.
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