- The role of fluorine in the stereoselective tandem aza-Michael addition to acrylamide acceptors: An experimental and theoretical mechanistic study
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Aza-Michael additions of αamino esters to fluorinated acceptors take place in a highly stereoselective manner, to give partially modified ψNHCH2]retropeptides incorporating a hydrolytically stable trifluoroalanine mimic. The reaction mechanism
- Fustero, Santos,Chiva, Gema,Piera, Julio,Volonterio, Alessandro,Zanda, Matteo,Gonzalez, Javier,Ramallal, Antonio Moran
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p. 8530 - 8542
(2008/04/01)
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- Highly stereoselective tandem aza-Michael addition-enolate protonation to form partially modified retropeptide mimetics incorporating a trifluoroalanine surrogate
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Fine-tuning of key reaction parameters, such as the solvent and the base used, led to a dramatic improvement in d.r. (from ≈1:1 to 38:1) in a tandem aza-Michael addition-enolate protonation sequence. Thus, the reaction of α-amino ester nucleophiles 1 with N-(α-trifiuoromethyl)acryloyl-α-amino ester acceptors 2 produced an array of partially modified retropeptide mimetics 3 with good to excellent stereocontrol (R, R1, R2, X, X1 = alkyl).
- Sani, Monica,Bruche, Luca,Chiva, Gema,Fustero, Santos,Piera, Julio,Volonterio, Alessandro,Zanda, Matteo
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p. 2060 - 2063
(2007/10/03)
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