Mechanochemical enzymatic resolution of N-benzylated-β3-amino esters

• Published in: Beilstein Journal of Organic Chemistry
• Main Authors: Mario Pérez-Venegas, Gloria Reyes-Rangel, Adrián Neri, Jaime Escalante, Eusebio Juaristi
• Format: Article in Journal/Newspaper
• Language: English
• Published: Beilstein-Institut 2017
• Subjects: ball-milling; β3-amino acid; Candida antarctica lipase B; enzymatic resolution; mechanochemistry; Science; Q; Organic chemistry; QD241-441; Antarc*; Antarctica
• Online Access: https://doi.org/10.3762/bjoc.13.167; https://doaj.org/article/9229156c47b24379871d5785d46db004

The use of mechanochemistry to carry out enantioselective reactions has been explored in the last ten years with excellent results. Several chiral organocatalysts and even enzymes have proved to be resistant to milling conditions, which allows for rather efficient enantioselective transformations under ball-milling conditions. The present article reports the first example of a liquid-assisted grinding (LAG) mechanochemical enzymatic resolution of racemic β3-amino esters employing Candida antarctica lipase B (CALB) to afford highly valuable enantioenriched N-benzylated-β3-amino acids in good yields. Furthermore the present protocol is readily scalable.