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

被引：24

作者：

Ueda, Jun ^{[1
]}

Harada, Shingo ^{[1
]}

Nakayama, Hiroki ^{[1
]}

Nemoto, Tetsuhiro ^{[1
,2
]}

机构：

[1] Chiba Univ, Grad Sch Pharmaceut Sci, Chuo Ku, 1-8-1 Inohana, Chiba 2608675, Japan

[2] Chiba Univ, Mol Chiral Res Ctr, Inage Ku, 1-33 Yayoi Cho, Chiba 2638522, Japan

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 25期

关键词：

N-H INSERTION; ASYMMETRIC CONJUGATE ADDITION; CARBENE MIGRATORY INSERTION; FORMAL AMIDE INSERTION; CHIRAL BRONSTED ACID; METAL-CARBENE; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; VINYLOGOUS REACTIVITY; GAMMA(2)-AMINO ACIDS;

D O I：

10.1039/c8ob00894a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple protocol to directly access -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.

引用

页码：4675 / 4682

页数：8

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