Stereoselective synthesis of 2-substituted 3-azabicyclo[3.2.0]heptan-2-ones by [2+2]-cycloaddition of N-allyl-beta-N-keteniminium salts derived from (R)-vinylglycinol

Authors
Delle Monache, G Misiti, D Salvatore, P Zappia, G Pierini, M
Citation
G. Delle Monache et al., Stereoselective synthesis of 2-substituted 3-azabicyclo[3.2.0]heptan-2-ones by [2+2]-cycloaddition of N-allyl-beta-N-keteniminium salts derived from (R)-vinylglycinol, TETRAHEDR-A, 11(13), 2000, pp. 2653-2659
Citations number
37
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
13
Year of publication
2000
Pages
2653 - 2659
Database
ISI
SICI code
0957-4166(20000714)11:13<2653:SSO23>2.0.ZU;2-1
Abstract
A stereoselective synthesis of (1R,2R,5S)-2-benzyloxymethyl-3-azabicyclo[3. 2.0]heptane-2-one was achieved, by intramolecular [2+2]-cycloaddition of (R )-vinylglycinol-derived N-allyl-beta-N-keteniminium salts, with high facial diastereoselection. The regio- and stereochemical courses have been qualit atively investigated by Molecular Mechanics calculations. (C) 2000 Elsevier Science Ltd. All rights reserved.