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Issue 89, 2015
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Enantioselective synthesis of fused heterocycles with contiguous stereogenic centers by chiral phosphoric acid catalyzed symmetry breaking

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Abstract

Described herein is a highly enantioselective synthesis of fused piperidine and pyrrolidine derivatives with all-carbon stereogenic centers. The enantioselective reductive amination from Cs-symmetric 1,3-dione derivatives proceeded in a highly stereoselective manner by taking advantage of the desymmetrization approach to afford fused heterocycles with contiguous stereogenic centers in good to excellent enantioselectivities (up to 98% ee).

Graphical abstract: Enantioselective synthesis of fused heterocycles with contiguous stereogenic centers by chiral phosphoric acid catalyzed symmetry breaking

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Article information


Submitted
04 Jul 2015
Accepted
14 Sep 2015
First published
14 Sep 2015

Chem. Commun., 2015,51, 16107-16110
Article type
Communication

Enantioselective synthesis of fused heterocycles with contiguous stereogenic centers by chiral phosphoric acid catalyzed symmetry breaking

K. Mori, A. Miyake and T. Akiyama, Chem. Commun., 2015, 51, 16107
DOI: 10.1039/C5CC05508C

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