Synthesis of Aryl Glycines by the a Arylation of Weinreb Amides

摘要

Aryl glycines are an important class of nonproteihogenic α-amino acids that are present in many drugs and natural products, such as glycopeptide antibiotics (e.g. vancomycin) and many β-lactam antibiotics (e.g. penicillins, cephalosporins, and nocardicins). Despite their deceptively simple structure, the enantioselective synthesis of aryl glycines is complicated by the ease of base-catalyzed racemization of the a stereocenter. As a result, many aryl glycines are synthesized in racemic form, and the enantiomers are then separated by resolution. During the last few decades, a wide range of racemic and asymmetric syntheses of aryl glycines have been developed. However, owing to the lack of generality and functional diversity of most of these methods, the generation of aryl glycines remains a challenge in organic chemistry.