Stereoselective synthesis of 2,3-disubstituted indoline diastereoisomers by chemoenzymatic processes.
Racemic indolines including a variety of structural motifs such as C-2 and C-3 substitutions (alkyl or aryl), cis/trans relative stereochemistry and functionalization of the aromatic ring (fluoro, methyl or methoxy groups) have been efficiently prepared through Fischer indolization and subsequent diastereoselective reduction of the unprotected indoles. Combination of  Candida antarctica  lipase type A and allyl 3-methoxyphenyl carbonate has been identified as the best tandem for their kinetic resolutions, observing excellent stereodiscriminations for most of the tested indolines.
Departamento de Química Orgánica e Inorgánica, Instituto Universitario de Biotecnología de Asturias, Universidad de Oviedo, 33006 Oviedo, Spain.
María
M
López-Iglesias
Eduardo
E
Busto
Vicente
V
Gotor
Vicente
V
Gotor-Fernández
D002175:Candida / Q000737:chemistry / Q000201:enzymology*; D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008049:Lipase / Q000737:chemistry* / Q000378:metabolism; D015394:Molecular Structure; D013237:Stereoisomerism
D007211:Indoles; C057812:indoline; D008049:Lipase