Enantioselective organocatalytic strategies to access noncanonical α-amino acids

Abstract

Organocatalytic asymmetric synthesis has evolved over the years and continues to attract the interest of many researchers worldwide. Enantiopure noncanonical amino acids (ncAAs) are valuable building blocks in organic synthesis,...

Backbone-Determined Antiarrhythmic Structure–Activity Relationships for a Mirror Image, Oligomeric Depsipeptide Natural Product

“…Since this analog campaign required ( S )-α-hydroxy heptanoic acid ester and amide preparation (e.g., 3 ), we chose to exploit the versatility of the Henry products, expecting that the nitroalkanes might bifurcate readily to a carboxylic acid for conventional ester and amide synthesis or be used directly to amide products (Figure ). , The development of a robust enantioselective synthesis of ( S )-α-hydroxy acid was a critical centerpiece and its use to prepare α-hydroxy benzyl ester 5 , N –H amide ( 3a ), and N –Me amide ( 3b ). An enantioselective synthesis of α-amino ester 7 for both N –H and N –Me functionality was equally critical.…”