Diastereoselective synthesis of psi[(E)-CH=CMe]- and psi[(Z)-CH=CMe]-type dipeptide isosteres by organocopper-mediated anti-S(N)2' reaction |
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| Authors: | Oishi Shinya Kamano Takae Niida Ayumu Odagaki Yoshihiko Tamamura Hirokazu Otaka Akira Hamanaka Nobuyuki Fujii Nobutaka |
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| Institution: | Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto, 606-8501, Japan. |
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| Abstract: | reaction: see text] Acyclic psi(E)-CH=CMe]- and psi(Z)-CH=CMe]-type dipeptide isosteres were efficiently synthesized. In a key reaction, alpha-alkylation of gamma-mesyloxy-beta-methyl-alpha,beta-unsaturated esters with organocyanocuprates in diethyl ether or tetrahydrofuran preferentially afforded the psi(E)-CH=CMe]- or psi(Z)-CH=CMe]-isomer, respectively, via anti-S(N)2' mechanism. |
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