Unprecedented formation of a benzo[d]azepine by acid-catalyzed cyclizationof a camphor-derived N-formylenamine

Authors
Meuzelaar, GJ Blom, A Maat, L Sheldon, RA
Citation
Gj. Meuzelaar et al., Unprecedented formation of a benzo[d]azepine by acid-catalyzed cyclizationof a camphor-derived N-formylenamine, EUR J ORG C, (2), 1999, pp. 519-522
Citations number
10
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
2
Year of publication
1999
Pages
519 - 522
Database
ISI
SICI code
1434-193X(199902):2<519:UFOABB>2.0.ZU;2-H
Abstract
A convenient synthesis of (-)-N-styryl-N-[2-(1,7,7-trimethyl-bicyclo[2.2.1] hept-2-enyl)ethyl]formamide (2) was developed starting from natural (+)-cam phor (3) via (-)-2-(bornen-2-yl)ethanol (6). Cyclization of the N-formylena mine 2 with the aid of 9-borabicyclo[3.3.1]non-9-yl triflate yielded a meth ano-bridged octahydro-1H-benzo[d]azepine derivative.