The first addition of silyl enol ethers to internal unactivated alkynes

Authors
Imamura, K Yoshikawa, E Gevorgyan, V Yamamoto, Y
Citation
K. Imamura et al., The first addition of silyl enol ethers to internal unactivated alkynes, TETRAHEDR L, 40(21), 1999, pp. 4081-4084
Citations number
23
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
21
Year of publication
1999
Pages
4081 - 4084
Database
ISI
SICI code
0040-4039(19990521)40:21<4081:TFAOSE>2.0.ZU;2-Z
Abstract
The EtAlCl2-mediated intramolecular addition of silyl enol ethers to both t erminal and internal unactivated alkynes, bearing alkyl and phenyl susbstit uents at the alkyne moiety, proceeded exclusively in the endo-fashion to gi ve mono- and bicyclic beta,gamma-unsaturated ketones in good to excellent y ields. The mechanism of this regiospecific Lewis acid-assisted carbocycliza tion is proposed, (C) 1999 Elsevier Science Ltd. All rights reserved.