Tandem chain extension–Mannich reaction: an approach to β-proline derivatives

AM Jacobine, ALA Puchlopek, CK Zercher, JB Briggs…

Index: Jacobine, Alexander M.; Puchlopek, Angela L.A.; Zercher, Charles K.; Briggs, Jon B.; Jasinski, Jerry P.; Butcher, Raymond J. Tetrahedron, 2012 , vol. 68, # 38 p. 7799 - 7805

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Citation Number: 6

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.