Short and efficient synthesis of enantiopure (+)-N-Boc-7-azabicyclo[2.2.1]heptan-2-one utilizing an asymmetric desymmetrization protocol: formal total synthesis of (-)-epibatidine

Authors
Pandey, C Tiwari, SK Singh, RS Mali, RS
Citation
C. Pandey et al., Short and efficient synthesis of enantiopure (+)-N-Boc-7-azabicyclo[2.2.1]heptan-2-one utilizing an asymmetric desymmetrization protocol: formal total synthesis of (-)-epibatidine, TETRAHEDR L, 42(23), 2001, pp. 3947-3949
Citations number
26
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
23
Year of publication
2001
Pages
3947 - 3949
Database
ISI
SICI code
0040-4039(20010604)42:23<3947:SAESOE>2.0.ZU;2-6
Abstract
A short and efficient synthesis of optically pure (+)-N-Boc-azabicyclo[2.2. 1]hept-2-one (2), a precursor in the synthesis of natural (-)-epibatidine ( 1), is reported by the asymmetric desymmetrization of meso-N-methoxycarbony l-2,3-bis(phenylsulfonyl)-7-azabicyclo[2.2.1]hept-2-ene (3). (C) 2001 Elsev ier Science Ltd. All rights Reserved.