Premium
Stereoselective Synthesis of Functionalized Pyrrolidines by the Diverted N−H Insertion Reaction of Metallocarbenes with β‐Aminoketone Derivatives
Author(s) -
Nicolle Simon M.,
Lewis William,
Hayes Christopher J.,
Moody Christopher J.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201511433
Subject(s) - chemistry , stereoselectivity , trifluoromethanesulfonate , aminoketone , aldol reaction , catalysis , porphyrin , rhodium , medicinal chemistry , stereochemistry , organic chemistry
A highly stereoselective route to functionalized pyrrolidines by the metal‐catalyzed diverted N−H insertion of a range of diazocarbonyl compounds with β‐aminoketone derivatives is described. A number of catalysts (rhodium(II) carboxylate dimers, copper(I) triflate, and an iron(III) porphyrin) are shown to promote the process under mild conditions to give a wide range of highly substituted proline derivatives. The reaction starts as a metallocarbene N−H insertion but is diverted by an intermolecular aldol reaction.