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Tandem chain extension-Mannich reaction: an approach to ?-proline derivatives.

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 ?-proline. The relative stereochemistry of the ?-proline can be controlled through use of different activating groups on the imine nitrogen.

SUBMITTER: Jacobine AM

PROVIDER: S-EPMC3489501 | biostudies-literature | 2012 Sep

REPOSITORIES: biostudies-literature

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

Jacobine Alexander M AM Puchlopek Angela L A AL Zercher Charles K CK Briggs Jon B JB Jasinski Jerry P JP Butcher Raymond J RJ

Tetrahedron 20120717 38

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. ...[more]

PMID: 23139434

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