title: Efficient access to enantiomerically pure cyclic alpha-amino esters through a lipase-catalyzed kinetic resolution.
abstract: A series of alpha-amino acid derivatives containing the 2,3-dihydroindole or octahydroindole core have been chemoenzymatically synthesized in good overall yields and high enantiomeric purity under mild reaction conditions using lipases for the introduction of chirality. Candida antarctica lipase type A has shown excellent activity and high enantiodiscrimination ability towards the two cyclic amino esters used as substrates. The selectivity of the process proved to be greatly dependent on the alkoxycarbonylating agent. Thus, the enzymatic kinetic resolution of methyl indoline-2-carboxylate has been successfully achieved using 3-methoxyphenyl allyl carbonate, whereas (2R,3aR,7aR)-benzyl octahydroindole-2-carboxylate required the less reactive diallyl carbonate.
authors.affiliation: Departamento de Química Orgánica e Inorgánica, Instituto Universitario de Biotecnología de Asturias, Universidad de Oviedo, 33071, Oviedo (Asturias), Spain.
authors.forename: Sergio
authors.initials: S
authors.lastname: Alatorre-Santamaría
authors.forename: María
authors.initials: M
authors.lastname: Rodriguez-Mata
authors.forename: Vicente
authors.initials: V
authors.lastname: Gotor-Fernández
authors.forename: Marcos Carlos
authors.initials: MC
authors.lastname: de Mattos
authors.forename: Francisco J
authors.initials: FJ
authors.lastname: Sayago
authors.forename: Ana I
authors.initials: AI
authors.lastname: Jiménez
authors.forename: Carlos
authors.initials: C
authors.lastname: Cativiela
authors.forename: Vicente
authors.initials: V
authors.lastname: Gotor