Total synthesis without protecting groups: pyrrolidines and cyclic carbamates.
A protecting group free synthesis of 2,3-cis substituted hydroxypyrrolidines is reported. Two novel reaction methodologies allow for the stereoselective formation of cyclic carbamates from olefinic amines, and the formation of primary amines via a Vasella/reductive amination reaction, both performed in aqueous media.
Dangerfield
Emma M
EM
Malaghan Institute of Medical Research, PO Box 7060, Wellington, New Zealand.
Timmer
Mattie S M
MS
Stocker
Bridget L
BL
D000586:Amination; D002219:Carbamates / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D002219:Carbamates; D011759:Pyrrolidines