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

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

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

Afiliação

Itoh K; Laboratory of Medicinal Chemistry, School of Pharmacy, Kitasato University 5-9-1 Shirokane, Minato-ku Tokyo 108-8641 Japan itok@pharm.kitasato-u.ac.jp.
Odate F; Medicinal Research Laboratories, School of Pharmacy, Kitasato University 5-9-1 Shirokane, Minato-ku Tokyo 108-8641 Japan.
Karikomi T; Applied Chemistry and Chemical Engineering Program, Graduate School, Kogakuin University 2665-1 Nakano Hachioji Tokyo 192-0015 Japan.
Obe K; Department of Applied Chemistry, Faculty of Engineering, Kogakuin University 2665-1 Nakano Hachioji Tokyo 192-0015 Japan.
Miyamori T; Department of Applied Chemistry, School of Advanced Engineering, Kogakuin University 2665-1 Nakano Hachioji Tokyo 192-0015 Japan.
Kamiya H; Department of Materials Chemistry, Faculty of Engineering, Shinshu University 4-17-1 Wakasato Nagano 380-8553 Japan.
Yoza K; Department of Materials Chemistry, Faculty of Engineering, Shinshu University 4-17-1 Wakasato Nagano 380-8553 Japan.
Nagai K; Bruker Japan 3-9, Moriya-cho, Kanagawa-ku Yokohama 221-0022 Japan.
Fujii H; Medicinal Research Laboratories, School of Pharmacy, Kitasato University 5-9-1 Shirokane, Minato-ku Tokyo 108-8641 Japan.
Suga H; Laboratory of Medicinal Chemistry, School of Pharmacy, Kitasato University 5-9-1 Shirokane, Minato-ku Tokyo 108-8641 Japan itok@pharm.kitasato-u.ac.jp.
Tokunaga K; Medicinal Research Laboratories, School of Pharmacy, Kitasato University 5-9-1 Shirokane, Minato-ku Tokyo 108-8641 Japan.

RSC Adv ; 9(22): 12365-12369, 2019 Apr 17.

Article em En | MEDLINE | ID: mdl-35515875

ABSTRACT

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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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: RSC Adv Ano de publicação: 2019 Tipo de documento: Article