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

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 un...

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Bibliographic Details
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
Description
Summary: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.

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