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Unprecedented Formation of a Benzo[ d ]azepine by Acid‐Catalyzed Cyclization of a Camphor‐Derived N ‐Formylenamine
Author(s) -
Meuzelaar Gerrit J.,
Blom Anders,
Maat Leendert,
Sheldon Roger A.
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199902)1999:2<519::aid-ejoc519>3.0.co;2-r
Subject(s) - chemistry , azepine , camphor , catalysis , derivative (finance) , formamide , ethanol , medicinal chemistry , organic chemistry , stereochemistry , financial economics , economics
A convenient synthesis of (–)‐ N ‐styryl‐ N ‐[2‐(1,7,7‐trimethylbicyclo[2.2.1]hept‐2‐enyl)ethyl]formamide ( 2 ) was developed starting from natural (+)‐camphor ( 3 ) via (–)‐2‐(bornen‐2‐yl)ethanol ( 6 ). Cyclization of the N ‐formylenamine 2 with the aid of 9‐borabicyclo[3.3.1]non‐9‐yl triflate yielded a methanobridged octahydro‐1 H ‐benzo[ d ]azepine derivative.