Chemoenzymatic preparation of optically active secondary amines: a new efficient route to enantiomerically pure indolines

An efficient chemoenzymatic route for the synthesis of optically active substituted indolines has been developed. Different lipases have been tested in the alkoxycarbonylation of these secondary amines, Candida antarctica lipase A (CAL-A) was found to be the best biocatalyst for 2-substituted-indoli...

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Bibliographic Details
Published in:Tetrahedron: Asymmetry
Main Authors: Gotor Fernández, Vicente, Fernández Torres, Pedro, Gotor Santamaría, Vicente Miguel
Format: Article in Journal/Newspaper
Language:English
Published: 2020
Subjects:
Cierva
Antarc*
Antarctica
Online Access:http://hdl.handle.net/10651/54880
https://doi.org/10.1016/j.tetasy.2006.08.012
Description
Summary:An efficient chemoenzymatic route for the synthesis of optically active substituted indolines has been developed. Different lipases have been tested in the alkoxycarbonylation of these secondary amines, Candida antarctica lipase A (CAL-A) was found to be the best biocatalyst for 2-substituted-indolines, and C. antarctica lipase B (CAL-B) for 3-methylindoline. The combination of lipases with a variety of allyl carbonates and tert-butyl methyl ether (TBME) as solvent has allowed the isolation of the carbamate and amine derivatives with a high level of enantiopurity Financial support of this work by the European Project EU-04-LSHB-2003-503017 is gratefully acknowledged. V.G.-F. thanks Ministerio de Educación y Ciencia for a personal grant (Juan de la Cierva Program).

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