TANDEM GENERATION AND INTRAMOLECULAR TRAPPING OF CHIRAL STABILIZED AZOMETHINE YLIDS WITH ALKYNE DIPOLAROPHILES

Authors
HARWOOD LM KITCHEN LC
Citation
Lm. Harwood et Lc. Kitchen, TANDEM GENERATION AND INTRAMOLECULAR TRAPPING OF CHIRAL STABILIZED AZOMETHINE YLIDS WITH ALKYNE DIPOLAROPHILES, Tetrahedron letters, 34(41), 1993, pp. 6603-6606
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
41
Year of publication
1993
Pages
6603 - 6606
Database
ISI
SICI code
0040-4039(1993)34:41<6603:TGAITO>2.0.ZU;2-R
Abstract
Due to the steric contraints imposed upon the bridging chain by the th ree-carbon linear unit associated with the alkyne, hex-5-ynal condense s with (5R)-phenylmorpholin-2-one (1), and undergoes intramolecular 32 dipolar cycloaddition via the syn- azomethine ylid to furnish adduct (2). This is in contrast to the anti-ylid pathway exhibited by the yl id derived from (1) and hept-6-ynal, which furnishes (6); or similar r eactions involving alkene dipolarophilic moieties.