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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


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.