Enantioselective synthesis of cyclopentane derivatives using zirconium-catalyzed asymmetric cyclization

Authors
Yamaura, Y Mori, M
Citation
Y. Yamaura et M. Mori, Enantioselective synthesis of cyclopentane derivatives using zirconium-catalyzed asymmetric cyclization, TETRAHEDR L, 40(16), 1999, pp. 3221-3224
Citations number
12
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
16
Year of publication
1999
Pages
3221 - 3224
Database
ISI
SICI code
0040-4039(19990416)40:16<3221:ESOCDU>2.0.ZU;2-V
Abstract
Cyclization of diene 2a using (S)-(EBTHI)ZrBINOL (1) (10 mol %) and BuMgCl in THF upon heating gave cyclopentane derivative trans-3a with 99% ee and c is-3a with 86% ee in 69% and 31% yields, respectively. In a similar manner, diene 10 gave cyclopentane derivative cis-11 with 94% ee in 81% yield as a sole product. (C) 1999 Elsevier Science Ltd. All rights reserved.