Remarkable interaction effects of molecular packing on site-and stereoselectivity in photocycloaddition of 2-pyrones with maleimide in the solid state

…, M Yasutake, T Shinmyozu, M Kawaminami, R Yoshida…

Index: Obata, Toru; Shimo, Tetsuro; Yasutake, Mikio; Shinmyozu, Teruo; Kawaminami, Masaru; Yoshida, Ryosuke; Somekawa, Kenichi Tetrahedron, 2001 , vol. 57, # 8 p. 1531 - 1541

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Citation Number: 30

Abstract

Solid-state photoirradiation of 1: 1 complex crystals of 4-[ω-(2-furyl) alkyloxy]-6-methyl-2- pyrones 1b, 1c or 4-(ω-arylalkyloxy)-6-methyl-2-pyrones 1d–j with maleimide 2 gave [2+ 2] cycloadducts 3b–f, 3i, 3j with exclusive stereoselectivity. The high reaction selectivity was confirmed by X-ray structure analyses and MO method of the complex crystals, which were composed of two sets of a 1: 1 complex between 1 and 2, arising from an CH–π ...