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Stereoselective Synthesis of Oxabicyclic Pyrrolidines of Medicinal Relevance: Merging Chemoenzymatic and Catalytic Methods
Author(s) -
Hocine Sofiane,
Montag Claire,
Reddy Vakiti Jithender,
Fourquez JeanMarie,
Hanessian Stephen
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001276
Subject(s) - enantiopure drug , chemistry , pyrrolidine , catalysis , ketone , stereoselectivity , organic chemistry , kinetic resolution , enantioselective synthesis , reagent , hydroamination , combinatorial chemistry , stereochemistry
Two approaches to the synthesis of an oxabicyclic pyrrolidine‐6‐one are described using enzymatic resolution and gold‐mediated catalysis as key steps toward enantiopure compounds previously reported as racemic mixtures. Addition of Grignard reagents to the ketone afforded a variety of diversified tertiary alcohols of interest for their reported pharmacological activities.