DOI: 10.1021/acs.orglett.6c04451 ISSN: 1523-7060
Catalytic Substrate- and Site-Selective Transesterification
Chengyi Shan, King Hung Nigel Tang, Kazumasa Kon, Masahiro Yamamoto, Makoto Yamashita, Kazuaki IshiharaAbstract
Substrate- and site-selective esterification is a powerful synthetic tool to reduce the number of steps required for the synthesis of complex molecules. To address the challenges associated with achieving such selectivity, a variety of strategies have been developed. However, these methods generally require highly reactive acylating reagents. We have developed the first catalytic process for a substrate- and site-selective transesterification using nonactivated esters as acylating reagents. The precisely engineered cavity surrounding the central metal in the sodium- and magnesium-based catalysts enables efficient steric discrimination between competing reaction sites.