[3 + 2] cycloaddition on carbohydrate templates: stereoselective synthesis of pyrrolidines.
Pyrrolidine derivatives were prepared in high diastereoselectivities and good yields via a [3 + 2] cycloaddition of a tert-butyldimethylsilyl protected carbohydrate-based allene with a diverse range of imines. The subsequent removal of the carbohydrate auxiliary afforded a variety of pyrrolidines with excellent enantioselectivities (up to 99% ee). Selective reduction of the pyrrolidines further demonstrated the potential of this strategy.
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore.
Shuting
S
Cai
Bala Kishan
BK
Gorityala
Jimei
J
Ma
Min Li
ML
Leow
Xue-Wei
XW
Liu
D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D012821:Silanes / Q000737:chemistry; D013237:Stereoisomerism
D002241:Carbohydrates; D011759:Pyrrolidines; D012821:Silanes