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: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Short Paper | Special issue | Vol 97, No. 1, 2018, pp.591-603
Published online, 17th May, 2018
DOI: 10.3987/COM-18-S(T)44
Lewis Acid Catalysis in Intermolecular [2+2] Photocycloaddition of Coumarin-3-carboxamide Bearing 2-Oxazolidinone Auxiliary with n-Propyl Vinyl Ether and Vinyl Pivalate

Kennosuke Itoh,* Junya Matsuura, Hideaki Kamiya, Ryuki Kudo, Yuki Takahashi, Yuta Hashimoto, Kenji Yoza, Ken Tokunaga,* Hideaki Fujii,* and Hiroyuki Suga*

*Laboratory of Medicinal Chemistry, School of Pharmacy, Kitasato University, 5-9-1, Shirokane, Minato-ku, Tokyo 108-8641, Japan

Abstract

Intermolecular [2+2] photocycloaddition reactions between 3-(2-oxo- 2H-chromene-3-carbonyl)oxazolidin-2-one with n-propyl vinyl ether and vinyl pivalate were carried out to give [2+2] cycloadducts in excellent yield with perfect regioselectivity. A Lewis acid catalyst (30 mol%) was moderately effective in accelerating the reaction. Furthermore, enantioselective reactions catalyzed by chiral Lewis acid catalysts (30 mol%) were performed to give cycloadducts in excellent yields with up to 13% ee.