Enzymatic resolution of (+/-)-cis- and (+/-)-trans-1-aminoindan-2-ol and (+/-)-cis- and (+/-)-trans-2-aminoindan-1-ol

Authors
Luna, A Maestro, A Astorga, C Gotor, V
Citation
A. Luna et al., Enzymatic resolution of (+/-)-cis- and (+/-)-trans-1-aminoindan-2-ol and (+/-)-cis- and (+/-)-trans-2-aminoindan-1-ol, TETRAHEDR-A, 10(10), 1999, pp. 1969-1977
Citations number
24
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
10
Year of publication
1999
Pages
1969 - 1977
Database
ISI
SICI code
0957-4166(19990521)10:10<1969:ERO(A(>2.0.ZU;2-J
Abstract
Pseudomonas cepacia lipase (PSL) efficiently catalyses the kinetic resoluti on of (+/-)-cis- and (+/-)-trans-1-aminoindan-2-ol through the O-acylation reaction of the corresponding N-benzyloxycarbonyl derivative using vinyl ac etate as the acyl donor. In a similar way, cis-N-Cbz-2-aminoindan-1-ol is r esolved when isopropenyl acetate is used as the acylating agent. The enanti oselectivity of the reaction was lower for (+/-)-trans-N-Cbz-2-aminoindan-1 -ol due to the different steric requirements for the two conformers of this substrate. (C) 1999 Elsevier Science Ltd. All rights reserved.