Silver-catalyzed regioselective hydroamination of alkenyl diazoacetates to synthesize Î³-amino acid equivalents.

Ueda, Jun; Harada, Shingo; Nakayama, Hiroki; Nemoto, Tetsuhiro

Ueda, Jun; Harada, Shingo; Nakayama, Hiroki; Nemoto, Tetsuhiro.

Afiliación

Ueda J; Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba 260-8675, Japan. Sharada@chiba-u.jp tnemoto@faculty.chiba-u.jp.
Harada S; Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba 260-8675, Japan. Sharada@chiba-u.jp tnemoto@faculty.chiba-u.jp.
Nakayama H; Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba 260-8675, Japan. Sharada@chiba-u.jp tnemoto@faculty.chiba-u.jp.
Nemoto T; Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba 260-8675, Japan. Sharada@chiba-u.jp tnemoto@faculty.chiba-u.jp and Molecular Chirality Research Center, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.

Org Biomol Chem ; 16(25): 4675-4682, 2018 07 07.

Article en En | MEDLINE | ID: mdl-29888358

RESUMEN

A simple protocol to directly access Î³-amino acid derivatives by intermolecular regioselective hydroamination of trichloroethyl alkenyldiazoacetates with carbamate using a silver tetrafluoroborate catalyst is described. Density functional theory (DFT) calculations to analyze the reaction mechanism revealed that multiple attractive interactions occur in a transition state to promote the vinylogous addition of nitrogen nucleophiles.

Texto completo

Imprimir

XML

PubMed Links

Buscar en Google

Texto completo: 1 Colección: 01-internacional Banco de datos: MEDLINE Idioma: En Revista: Org Biomol Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2018 Tipo del documento: Article

Texto completo

Imprimir

XML

PubMed Links

Buscar en Google