Premium
Candida antarctica lipase‐B‐catalyzed kinetic resolution of 1,3‐dialkyl‐3‐hydroxymethyl oxindoles
Author(s) -
Kumar Naveen,
Kumar Akshay,
Sahoo Subash Chandra,
Chimni Swapandeep Singh
Publication year - 2020
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.23284
Subject(s) - candida antarctica , chemistry , hydroxymethyl , kinetic resolution , synthon , oxindole , lipase , catalysis , furan , stereochemistry , acetonitrile , organic chemistry , enantioselective synthesis , enzyme
Abstract Candida antarctica (CAL‐B) lipase‐catalyzed resolution of 1,3‐dialkyl‐3‐hydroxymethyl oxindoles has been performed to obtain ( R )‐1,3‐dialkyl‐3‐acetoxymethyl oxindoles with up to 99% ee and ( S )‐1,3‐dialkyl‐3‐hydroxymethyl oxindoles with up to 78% ee using vinyl acetate as acylating agent and acetonitrile as solvent transforming ( S )‐3‐allyl‐3‐hydroxymethyl oxindole to (3 S )‐1′‐benzyl‐5‐(iodomethyl)‐4,5‐dihydro‐2 H ‐spiro[furan‐3,3′‐indolin]‐2′‐one. The optically active 3‐substituted‐3‐hydroxymethyl oxindoles and spiro‐oxindoles are among the key synthons in the synthesis of potentially biologically active molecules.