379699-75-9Relevant academic research and scientific papers
Aqueous organocatalyzed aldol reaction of glyoxylic acid for the enantioselective synthesis of α-hydroxy-γ-keto acids
Moles, Fernando J. N.,Guillena, Gabriela,Najera, Carmen
, p. 9963 - 9966 (2014)
N-Tosyl-(Sa)-binam-l-prolinamide is an efficient catalyst for the aqueous aldol reaction, between glyoxylic acid, as monohydrate or aqueous solution, and ketones. This reaction led to the formation of chiral α-hydroxy-γ-keto carboxylic acids in
Glyoxylic acid versus ethyl glyoxylate for the aqueous enantio selective Synthesis of α-hydroxy-γ-keto acids and esters by the N-Tosyl-(S a)-binam-l-prolinamide-organocatalyzed aldol reaction
Moles, Fernando J. N.,Guillena, Gabriela,Njera, Carmen,Gmez-Bengoa, Enrique
supporting information, p. 549 - 561 (2015/02/19)
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.
