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Synthesis 2015; 47(04): 549-561
DOI: 10.1055/s-0034-1379546
DOI: 10.1055/s-0034-1379546
paper
Glyoxylic Acid versus Ethyl Glyoxylate for the Aqueous Enantioselective Synthesis of α-Hydroxy-γ-Keto Acids and Esters by the N-Tosyl-(S a)-binam-l-prolinamide-Organocatalyzed Aldol Reaction
Further Information
Publication History
Received: 13 August 2014
Accepted after revision: 28 October 2014
Publication Date:
27 November 2014 (online)
Abstract
N-Tosyl-(S a)-binam-l-prolinamide is an efficient catalyst for the aqueous aldol reaction between ketones and glyoxylic acid, as the monohydrate or as an aqueous solution, or a 50% toluene solution of ethyl glyoxylate. These reactions led to the formation of chiral α-hydroxy-γ-keto carboxylic acids and esters in high levels of diastereo- and enantioselectivities (up to 97% ee), providing mainly anti aldol products. Only cyclopentanone and cyclohexane-1,4-dione afforded an almost 1:1 mixture of the syn/anti-diastereoisomers; however, the reaction between 4-phenylcyclohexanone and ethyl glyoxylate gave the corresponding syn,syn-product as the major diastereoisomer.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379546.
- Supporting Information
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