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. 2012 Sep 23;68(38):7799-7805.
doi: 10.1016/j.tet.2012.07.039. Epub 2012 Jul 17.

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

Alexander M Jacobine  1 , Angela L A Puchlopek, Charles K Zercher, Jon B Briggs, Jerry P Jasinski, Raymond J Butcher
Affiliations

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

Alexander M Jacobine et al. Tetrahedron. .

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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Figures

Figure 1
Figure 1
Divergent Diastereocontrol based upon Imines
Scheme 1
Scheme 1
Tandem Chain Extension-Mannich reaction with Sulfinimine 3
Scheme 2
Scheme 2
Tandem Chain Extension-Mannich Reaction with Diphenylphosphinoyl Imine 6
Scheme 3
Scheme 3
Formation of racemic β-proline derivatives 12 through use of N-Boc imines 9
Scheme 4
Scheme 4
Synthesis of β-proline derivative 18 from β-keto imide 16
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