Asymmetric synthesis of 2-arylpyrrolidines starting from gamma-chloro N-(tert-butanesulfinyl)ketimines.
The enantioselective reductive cyclization of gamma-chloro N-(tert-butanesulfinyl)ketimines towards the short and efficient synthesis of (S)- and (R)-2-arylpyrrolidines (ee >99%) is described for the first time by treatment with LiBEt(3)H and subsequent acid deprotection.
Leemans
Erika
E
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
Mangelinckx
Sven
S
De Kimpe
Norbert
N
D003500:Cyclization; D007097:Imines / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D007097:Imines; D009570:Nitriles; D011759:Pyrrolidines; C542835:ketimine