EXCELLENT STEREOCONTROL IN INTRAMOLECULAR BUCHNER CYCLIZATIONS AND SUBSEQUENT CYCLOADDITIONS - STEREOSPECIFIC CONSTRUCTION OF POLYCYCLIC SYSTEMS

Authors
MAGUIRE AR BUCKLEY NR OLEARY P FERGUSON G
Citation
Ar. Maguire et al., EXCELLENT STEREOCONTROL IN INTRAMOLECULAR BUCHNER CYCLIZATIONS AND SUBSEQUENT CYCLOADDITIONS - STEREOSPECIFIC CONSTRUCTION OF POLYCYCLIC SYSTEMS, Chemical communications, (22), 1996, pp. 2595-2596
Citations number
11
Categorie Soggetti
Chemistry
Journal title
Chemical communications → ACNP
ISSN journal
13597345
Issue
22
Year of publication
1996
Pages
2595 - 2596
Database
ISI
SICI code
1359-7345(1996):22<2595:ESIIBC>2.0.ZU;2-R
Abstract
Highly diastereoselective rhodium(II) acetate-catalysed intramolecular addition of alpha-diazo ketones to aromatic rings to form the azuleno nes 3 has been achieved; the norcaradiene form of 3 undergoes efficien t stereospecific cycloaddition with phenyltriazolinedione, in either a stepwise or a tandem process, leading to the pentacyclic systems 4 as a single diastereomer in each case.