Tandem Chain Extension-Mannich Reaction: An Approach to β-Proline Derivatives

Authors

Alexander M. Jacobine, University of New Hampshire
Angela L. A. Puchlopek, University of New Hampshire
Charles K. Zercher, University of New HampshireFollow
Jonathan B. Briggs, University of New HampshireFollow
Jerry P. Jasinski, Keene State CollegeFollow
Ray J. Butcher, Howard UniversityFollow

Abstract

A zinc carbenoid-initiated chain extension reaction provides access to an organometallic intermediate, which can be used to capture activated imines. Deprotection of the nitrogen and reduction provides access to racemic derivatives of β-proline. The relative stereochemistry of the β-proline can be controlled through use of different activating groups on the imine nitrogen.

Department

Chemistry

Publication Date

9-23-2012

Journal Title

Tetrahedron

Publisher

Elsevier

Digital Object Identifier (DOI)

10.1016/j.tet.2012.07.039

Document Type

Article

Recommended Citation

Tandem Chain Extension-Mannich Reaction: An Approach to β-Proline Derivatives, Jacobine, A. M.; Puchlopek, A. L. A.; Zercher, C. K.; Briggs, J. B.; Jasinski, J. P.; Butcher, R. J. Tetrahedron 2012, 68, 7799–7805. (Highlighted in SynFacts 2012, 8, 1121.)

Rights

Copyright © 2012, Elsevier