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Tandem chain extension-Mannich reaction: an approach to β-proline derivatives
Alexander M Jacobine1, Angela L A Puchlopek, Charles K Zercher
1Department of Chemistry, University of New Hampshire, Durham, NH 03824.
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.
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