642410-76-2Relevant academic research and scientific papers
New Diastereoselective Route to 2-Substituted cis-(2S,5S)- and trans-(2S,5R)-5-Alkylpyrrolidines as Indolizidine and Pyrrolizidine Scaffolds
Mota, Antonio J.,Chiaroni, Angele,Langlois, Nicole
, p. 4187 - 4198 (2007/10/03)
A new and short stereoselective route to the synthesis of enantiopure cis-2,5-disubstituted pyrrolidines as indolizidine or pyrrolizidine scaffolds has been developed. The method, which uses (S)-pyroglutamic acid as a chiral starting material, is based on the ring opening of N-protected 7-lactams by alkyl phenyl sulfone carbanions, followed by desulfonylation and reductive amination of alkyl 7-amino ketones. The diastereoselectivity depends on the substitution of the starting γ-lactams, and on the alkyl group of the phenyl sulfone. Total cis diastereoselectivity was observed in the formation of tert-butyl 5-alkylprolinates. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
