Chiral cycloalkylidene alpha,beta-unsaturated iminium approach to stereoselective formal [3+3] cycloaddition reaction in spiroheterocycle synthesis

Authors
McLaughlin, MJ Shen, HC Hsung, RP
Citation
Mj. Mclaughlin et al., Chiral cycloalkylidene alpha,beta-unsaturated iminium approach to stereoselective formal [3+3] cycloaddition reaction in spiroheterocycle synthesis, TETRAHEDR L, 42(4), 2001, pp. 609-613
Citations number
27
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
4
Year of publication
2001
Pages
609 - 613
Database
ISI
SICI code
0040-4039(20010122)42:4<609:CCAIAT>2.0.ZU;2-W
Abstract
An approach to stereoselective formal [3+3] cycloaddition reaction using ch iral cycloalkylidene alpha,beta -unsaturated iminiums is described here lea ding to preparations of spiroheterocycles in modest stereoselectivity. The reversibility of 6 pi -electron electrocyclic ring closure did not always l ead to the thermodynamically more favored product. These observations led t o other useful mechanistic understanding of electrocyclic ring closure of 1 -oxatrienes. (C) 2001 Elsevier Science Ltd. All rights reserved.