Organocatalytic Enantioselective Decarboxylative Addition of Malonic Half Thioesters to Imines

DOI Web Site Web Site 8 Citations

Description

<jats:title>Abstract</jats:title><jats:p>We describe a biomimetic organocatalytic enantioselective decarboxylative addition of malonic acid half thioesters to imines. This simple protocol makes use of readily available <jats:italic>Cinchona</jats:italic>‐derived organocatalysts and nucleophiles at the carboxylate oxidation state. The resulting β‐amino thioesters, being attractive precursors for the preparation of optically active β‐amino acids, are formed in good yields and in up to 79 % <jats:italic>ee</jats:italic>. As suggested by several mechanistic insights the desired products are formed <jats:italic>via</jats:italic> initial formation of a thioester acetate enolate <jats:italic>via</jats:italic> decarboxylation of the malonic acid half thioester, followed by addition to the imine.</jats:p>

Journal

Citations (8)*help

See more

Report a problem

Back to top