Desymmetrisation of a meso-N-hydroxyimide via a chiral Lossen reaction

Authors
Chandrasekhar, S Sridhar, M
Citation
S. Chandrasekhar et M. Sridhar, Desymmetrisation of a meso-N-hydroxyimide via a chiral Lossen reaction, TETRAHEDR-A, 11(17), 2000, pp. 3467-3469
Citations number
5
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
17
Year of publication
2000
Pages
3467 - 3469
Database
ISI
SICI code
0957-4166(20000908)11:17<3467:DOAMVA>2.0.ZU;2-4
Abstract
N-[(1S)-10-Camphorsulphonyloxy]norborn-5-ene-endo-2,3-dicarboximide 2 under went a Lossen type reaction with dicyclohexylmethylamine to furnish endo-2- methoxycarbonyl-endo-3-(methoxycarbonyl-amino)norborn-5-ene 3, in 84% yield and 33% e.e. (by NMR). (C) 2000 Elsevier Science Ltd. All rights reserved.