Hydroxy direction of zinc carbenoid addition to a remote olefin. Analysis and improvement of 2,4-pentanediol tethered Furukawa cyclopropanation

Authors
Sugimura, T Futagawa, T Yoshikawa, M Katagiri, T Miyashige, R Mizuguchi, M Nagano, S Sugimori, S Tai, A Tei, T Okuyama, T
Citation
T. Sugimura et al., Hydroxy direction of zinc carbenoid addition to a remote olefin. Analysis and improvement of 2,4-pentanediol tethered Furukawa cyclopropanation, TETRAHEDRON, 57(35), 2001, pp. 7495-7499
Citations number
25
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
35
Year of publication
2001
Pages
7495 - 7499
Database
ISI
SICI code
0040-4020(20010827)57:35<7495:HDOZCA>2.0.ZU;2-Z
Abstract
Zinc carbenoid addition to an olefin stereocontrolled by a chiral and remot e intramolecular hydroxy group was studied in detail. Stereoselectivity as well as chemical yield of the Furukawa cyclopropanation was dramatically im proved by modifications of the procedure of addition of the reagents. The s tructure of an active species to give the hydroxy-directed product is propo sed. (C) 2001 Elsevier Science Ltd. All rights reserved.