Stereoselective Synthesis of Functionalized Pyrrolidines by the Diverted N−H Insertion Reaction of Metallocarbenes with β‐Aminoketone Derivatives. (5th February 2016)

• Record Type: Journal Article
• Authors: Nicolle, Simon M.; Lewis, William; Hayes, Christopher J.; Moody, Christopher J.
• Is Part Of: Angewandte Chemie. Volume 128:Number 11(2016)
• Page Start: 3813
• Page End: 3817
• Publication Date: 2016-02-05
• Subjects: Aldolreaktionen -- Carbene -- Diazoverbindungen -- Stickstoffheterocyclen -- Übergangsmetallkatalyse; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201511433
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: 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.