Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,320 (Yen only)
Period: This Article can be accessed for 7 days.

Communication | Special issue | Vol 79, No. 1, 2009, pp.353-358
Published online, 23rd October, 2008
DOI: 10.3987/COM-08-S(D)22
Stereoselective Synthesis of 5-Substituted 2-Allyl-3-oxotetrahydrofuran-2-carboxylates Using Rhodium(II)-Catalyzed Oxonium Ylide Formation–[2,3] Shift

Takayuki Yakura,* Katsuaki Matsui, Kazumasa Matsuzaka, and Masayuki Yamashita

*Faculty of Pharmaceutical Sciences, Graduate School, Toyama University, 2630 Sugitani, Toyama, Toyama 930-0194, Japan

Abstract

Reaction of 5-allyloxy-2-diazo-3-ketoesters 1 with catalytic amount of dirhodium(II) tetraacetate in dichloromethane proceeded in high yields with excellent stereoselectivities to give methyl 5-substituted 2-allyl-3-oxotetrahydro- furan-2-carboxylates 2, which are suitable intermediates for synthesis of heliespirones and their derivatives.