Combining Chiral Aldehyde Catalysis and Transition-Metal Catalysis for Enantioselective α-Allylic Alkylation of Amino Acid Esters

被引：77

作者：

Chen, Lei ^{[1
,2
]}

Luo, Ming-Jing ^{[1
,2
]}

Zhu, Fang ^{[1
,2
]}

Wen, Wei ^{[1
,2
]}

Guo, Qi-Xiang ^{[1
,2
]}

机构：

[1] Southwest Univ, Key Lab Appl Chem Chongqing Municipal, Sch Chem & Chem Engn, Chongqing 400715, Peoples R China

[2] Southwest Univ, Chongqing Key Lab Soft Matter Mat Chem & Funct Mf, Sch Chem & Chem Engn, Chongqing 400715, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2019年 / 141卷 / 13期

关键词：

ASYMMETRIC ALLYLATION; PALLADIUM; ORGANOCATALYSIS; ACCESS; HYDROAMINATION; PYRIDOXAL; STRATEGY; LIGAND;

D O I：

10.1021/jacs.9b01910

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A chiral aldehyde is rationally combined with a Lewis acid and a transition metal for the first time to form a triple catalytic system. This cocatalytic system exhibits good catalytic activation and stereoselective-control abilities in the asymmetric alpha-allylation reaction of N-unprotected amino acid esters and allyl acetates. Optically active alpha,alpha-disubstituted a-amino acids (alpha-AAs) are generated in good yields (up to 87%) and enantioselectivities (up to 96% ee). Preliminary mechanism investigation indicates that the chiral aldehyde 3f acts both as an organocatalyst to activate the amino acid ester via the formation of a Schiff base, and as a ligand to facilitate the nucleophilic attack process by coordinating with pi-allyl Pd(II) species.

引用

页码：5159 / 5163

页数：5

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