A fast, efficient and stereoselective synthesis of hydroxy-pyrrolidines.
A five-step, protecting group free synthesis of 2,3-cis substituted hydroxy-pyrrolidines is presented. Key steps in the synthesis are the chemoselective formation of a primary amine via a Vasella reductive amination using ammonia as the nitrogen source, and the stereoselective formation of a cyclic carbamate from an alkenylamine. Improvement of the reductive amination, by way of the use of alpha-picoline borane as a more environmentally benign reducing agent, is also presented.
Dangerfield
Emma M
EM
Malaghan Institute of Medical Research, PO Box 7060, Wellington, New Zealand.
Gulab
Shivali A
SA
Plunkett
Catherine H
CH
Timmer
Mattie S M
MS
Stocker
Bridget L
BL
D000586:Amination; D002219:Carbamates / Q000737:chemistry; D007700:Kinetics; D010084:Oxidation-Reduction; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D014993:Xylitol / Q000737:chemistry
D002219:Carbamates; D011759:Pyrrolidines; C032519:pyrrolidine; D014993:Xylitol