Diastereo- and Enantioselective Synthesis of Quaternary α-Amino Acid Precursors by Copper -Catalyzed Propargylation

被引：32

作者：

Zhu, Qiongqiong ^{[1
,2
]}

Meng, Beibei ^{[1
,2
]}

Gu, Congzheng ^{[1
,2
]}

Xu, Ye ^{[1
,2
]}

Chen, Jie ^{[1
,2
]}

Lei, Chuanhu ^{[1
,2
]}

Wu, Xiaoyu ^{[1
,2
,3
]}

机构：

[1] Shanghai Univ, Coll Sci, Ctr Supramol Chem & Catalysis, 99 Shangda Lu, Shanghai 200444, Peoples R China

[2] Shanghai Univ, Coll Sci, Dept Chem, 99 Shangda Lu, Shanghai 200444, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, 345 Lingling Lu, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 24期

基金：

中国国家自然科学基金;

关键词：

ASYMMETRIC-SYNTHESIS; BETA-KETOESTERS; ESTERS; CYCLOADDITION; CONSTRUCTION; COMPLEXES; LIGANDS;

D O I：

10.1021/acs.orglett.9b03894

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A diastereo- and enantioselective propargylic substitution reaction between propargylic carbonates and asubstituted nitroacetates catalyzed by a Cu pybox complex is described. This method allows the preparation of a series of non-proteinogenic quaternary a-amino acid precursors featuring two contiguous stereogenic centers and a terminal alkyne moiety in high yields with good to excellent diastereo- and enantioselectivities in most cases. The propargylated adducts were elaborated into a diverse set of quaternary a -amino acid derivatives.

引用

页码：9985 / 9989

页数：5

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