Stereoselective syn aldol reaction of the lithium ester enolate of ethyl N,N-dimethylglycine in the presence of triethylborane

Add time:08/03/2019    Source:sciencedirect.com

Aldol condensation of acetaldehyde and benzaldehyde with the lithium ester enolate of ethyl N,N-dimethylglycine in the presence of one equivalent of triethylborane resulted in the formation of the corresponding 3-hydroxy-2-amino acid ester with excellent stereocontrol (>95% de ) for the formation of syn products. The stereochemical outcome of these reactions is rationalized via the selective formation of the (Z)-enolate of 1 in the presence of triethylborane.

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