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

共 50 条

[41] Diastereo- and enantioselective synthesis of β-amino cyclic ethers via the intramolecular reaction of γ-alkoxyallylstannane with imine
Park, JY
Kadota, I
Yamamoto, Y
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (13): : 4901 - 4908
[42] Catalytic Diastereo- and Enantioselective Synthesis of 2-Imidazolinones
Martinez-Pardo, Pablo
Blay, Gonzalo
Escriva-Palomo, Alba
Sanz-Marco, Amparo
Vila, Carlos
Pedro, Jose R.
ORGANIC LETTERS, 2019, 21 (11) : 4063 - 4066
[43] Diastereo- and enantioselective synthesis of N,O-nucleosides
Chiacchio, U
Corsaro, A
Iannazzo, D
Piperno, A
Pistarà, V
Rescifina, A
Romeo, R
Sindona, G
Romeo, G
TETRAHEDRON-ASYMMETRY, 2003, 14 (18) : 2717 - 2723
[44] Diastereo- and enantioselective synthesis of (+)- and (-)-cis-2-aminocyclobutanols
Bisel, P
Breitling, E
Frahm, AW
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1998, 1998 (04) : 729 - 733
[45] Diastereo- and enantioselective synthesis of dimethylcyclohexanamines by asymmetric reductive amination
Speckenbach, B
Bisel, P
Frahm, AW
SYNTHESIS-STUTTGART, 1997, (11): : 1325 - 1330
[46] Diastereo- and enantioselective synthesis of a conagenin skeletal amide moiety
Augusto, J
Rodrigues, R
Moran, PJS
Milagre, CDF
Ursini, CV
TETRAHEDRON LETTERS, 2004, 45 (18) : 3579 - 3582
[47] Enzymatic diastereo- and enantioselective synthesis of α-alkyl-α,β-dihydroxyketones
Giovannini, Pier Paolo
Fantin, Giancarlo
Massi, Alessandro
Venturi, Valentina
Pedrini, Paola
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (23) : 8038 - 8045
[48] Bifunctional Amino Sulfonohydrazide Catalyzed Direct Asymmetric Mannich Reaction of Cyclic Ketimines with Ketones: Highly Diastereo- and Enantioselective Construction of Quaternary Carbon Stereocenters
Zhang, Sheng
Li, Lijun
Hu, Yanbin
Zha, Zhenggen
Wang, Zhiyong
Loh, Teck-Peng
ORGANIC LETTERS, 2015, 17 (04) : 1050 - 1053
[49] Diastereo- and Enantioselective Synthesis of Fluorinated Proline Derivatives via Copper(I)-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition
Li, Qing
Ding, Chang-Hua
Li, Xiao-Hui
Weissensteiner, Walter
Hou, Xue-Long
SYNTHESIS-STUTTGART, 2012, 44 (02): : 265 - 271
[50] A Highly Diastereo- and Enantioselective Copper(I)-Catalyzed Henry Reaction Using a Bis(sulfonamide)-Diamine Ligand
Jin, Wei
Li, Xincheng
Wan, Boshun
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (02): : 484 - 491

← 1 2 3 4 5 →