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New tartrate based cyclic phosphoric acids as organocatalysts in Mannich reactions

New tartrate based cyclic phosphoric acids as organocatalysts in Mannich reactions Abstract Cyclic phosphoric acids have attracted much attention as chiral organocatalysts. While binaphthol based ligands have been extensively used in various transformations, the analogous TADDOL-type ligands are less explored. A library of seventeen cyclic phosphoric acids with structural variation of the TADDOL backbone were synthesized and an optimization study of the Mannich reaction of aromatic N-(2-hydroxyphenyl)imines with 2,2-dimethyl-1-methoxy-silylenolate was performed. Enantioselectivities between 96% (S) and 70% (R) were observed and a rationalisation, based on crystal structure analysis and DFT calculations, is provided. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Asymmetric Catalysis de Gruyter

New tartrate based cyclic phosphoric acids as organocatalysts in Mannich reactions

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References (53)

Publisher
de Gruyter
Copyright
Copyright © 2016 by the
ISSN
2300-4630
eISSN
2300-4630
DOI
10.1515/asorg-2016-0001
Publisher site
See Article on Publisher Site

Abstract

Abstract Cyclic phosphoric acids have attracted much attention as chiral organocatalysts. While binaphthol based ligands have been extensively used in various transformations, the analogous TADDOL-type ligands are less explored. A library of seventeen cyclic phosphoric acids with structural variation of the TADDOL backbone were synthesized and an optimization study of the Mannich reaction of aromatic N-(2-hydroxyphenyl)imines with 2,2-dimethyl-1-methoxy-silylenolate was performed. Enantioselectivities between 96% (S) and 70% (R) were observed and a rationalisation, based on crystal structure analysis and DFT calculations, is provided.

Journal

Asymmetric Catalysisde Gruyter

Published: Sep 12, 2016

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