Novel asymmetric photodimerization reaction of coumarin derivatives bearing a chiral 2-oxazolidinone auxiliary

Kennosuke Itoh; Fumiya Odate; Takuma Karikomi; Keishi Obe; Tsutomu Miyamori; Hideaki Kamiya; Kenji Yoza; Kenichiro Nagai; Hideaki Fujii; Hiroyuki Suga; Ken Tokunaga

doi:10.1039/C9RA00822E

Novel asymmetric photodimerization reaction of coumarin derivatives bearing a chiral 2-oxazolidinone auxiliary†

Kennosuke Itoh,

*^ab Fumiya Odate,^c Takuma Karikomi,^d Keishi Obe,^e Tsutomu Miyamori,^f Hideaki Kamiya,^f Kenji Yoza,^g Kenichiro Nagai,

^b Hideaki Fujii,

*^ab Hiroyuki Suga

*^f and Ken Tokunaga

*^h

Author affiliations

* Corresponding authors

^a Laboratory of Medicinal Chemistry, School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan
E-mail: itok@pharm.kitasato-u.ac.jp

^b Medicinal Research Laboratories, School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan

^c Applied Chemistry and Chemical Engineering Program, Graduate School, Kogakuin University, 2665-1 Nakano, Hachioji, Tokyo 192-0015, Japan

^d Department of Applied Chemistry, Faculty of Engineering, Kogakuin University, 2665-1 Nakano, Hachioji, Tokyo 192-0015, Japan

^e Department of Applied Chemistry, School of Advanced Engineering, Kogakuin University, 2665-1 Nakano, Hachioji, Tokyo 192-0015, Japan

^f Department of Materials Chemistry, Faculty of Engineering, Shinshu University, 4-17-1 Wakasato, Nagano 380-8553, Japan

^g Bruker Japan, 3-9, Moriya-cho, Kanagawa-ku, Yokohama 221-0022, Japan

^h Division of Liberal Arts, Center for Promotion of Higher Education, Kogakuin University, 2665-1 Nakano, Hachioji, Tokyo 192-0015, Japan

Abstract

A novel asymmetric photodimerization reaction of coumarin derivatives bearing the (S)-4-benzyl-2-oxazolidinone auxiliary provides only the syn-head-to-tail (syn-HT) dimer with moderate diastereoselectivity (up to 75 : 25). The mechanism of complete syn-HT selectivity and moderate diastereoselectivity is proposed based on the result of density functional theory (DFT) calculation. The benzyl group of the (S)-4-benzyl-2-oxazolidinone auxiliary in combination with a Lewis acid exerts effective diastereofacial shielding of the reaction site.

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Novel asymmetric photodimerization reaction of coumarin derivatives bearing a chiral 2-oxazolidinone auxiliary†

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Novel asymmetric photodimerization reaction of coumarin derivatives bearing a chiral 2-oxazolidinone auxiliary

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