Journal
TETRAHEDRON-ASYMMETRY
Volume 25, Issue 18-19, Pages 1323-1330Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2014.08.012
Keywords
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Funding
- Spanish Ministerio de Economia y Competitividad (MINECO) [CTQ2010-20387, CSD2007-00006]
- FEDER
- Generalitat Valenciana [Prometeo/2009/039]
- University of Alicante
- European Commission [ORCA action CM0905]
- Spanish MINECO [FPU AP2009-3601]
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Aqueous 2,2-dimethoxyacetaldehyde (60% wt solution) is used as an acceptor in aldol reactions, with cyclic and acyclic ketones and aldehydes as donors, organocatalyzed by 10 mol % of N-tosyl-(S-a)-binam-L-prolinamide [(S-a)-binam-sulfo-L-Pro] at it under solvent-free conditions. The corresponding monoprotected 2-hydroxy-1,4-dicarbonyl compounds are obtained in good yields and with high levels of diastereo- and enantioselectivity mainly as anti-aldols. In the case of 4-substituted cyclohexanones a desymmetrization process takes place to mainly afford the anti,anti-aldols. 2,2-Dimethyl-1,3-dioxan-5-one allows the synthesis of a useful intermediate for the preparation of carbohydrates in higher yield, de and ee than with L-Pro as the organocatalyst. (C) 2014 Elsevier Ltd. All rights reserved.
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