Chiral Primary Amine/Palladium Dual Catalysis for Asymmetric Allylic Alkylation of β-Ketocarbonyl Compounds with Allylic Alcohols

被引：93

作者：

Zhou, Han ^{[1
]}

Zhang, Long ^{[1
]}

Xu, Changming ^{[1
]}

Luo, Sanzhong ^{[1
]}

机构：

[1] Chinese Acad Sci, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 43期

关键词：

allylic alcohols; asymmetric allylic alkylation; chiral primary amines; palladium; beta-ketocarbonyl compounds; TRANSITION-METAL; ENAMINE CATALYSIS; ALPHA-ALLYLATION; PHOSPHORIC-ACID; BOND-CLEAVAGE; PALLADIUM; ALDEHYDES; LIGANDS; COMBINATION; ACTIVATION;

D O I：

10.1002/anie.201505946

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient dual catalytic system composed of a chiral primary amine and a palladium complex was developed to promote the direct asymmetric allylic alkylation (AAA) of beta-ketocarbonyl compounds. In particular, the synergistic dual catalytic system enabled the AAA reaction of challenging acyclic aliphatic ketones, such as b-ketocarbonyl compounds and 1,3-diketones.

引用

页码：12645 / 12648

页数：4

共 50 条

[21] Tandem Thorpe Reaction/Palladium Catalyzed Asymmetric Allylic Alkylation: Access to Chiral -enaminonitriles with Excellent Enantioselectivity [J].

Bai, Da-Chang ;

Liu, Xiu-Yan ;

Li, Hao ;

Ding, Chang-Hua ;

Hou, Xue-Long .

CHEMISTRY-AN ASIAN JOURNAL, 2017, 12 (02) :212-215

[22] Enamines: efficient nucleophiles for the palladium-catalyzed asymmetric allylic alkylation [J].

Zhao, Xiaohu ;

Liu, Delong ;

Xie, Fang ;

Zhang, Wanbin .

TETRAHEDRON, 2009, 65 (02) :512-517

[23] Application of sSPhos as a Chiral Ligand for Palladium-Catalyzed Asymmetric Allylic Alkylation [J].

Docherty, Philip J. ;

Kadarauch, Max ;

Mistry, Nisha ;

Phipps, Robert J. .

ORGANIC LETTERS, 2023, 26 (14) :2862-2866

[24] Recent Advances on the Catalytic Asymmetric Allylic α-Alkylation of Carbonyl Derivatives Using Free Allylic Alcohols [J].

Alonso, Diego A. ;

Macia, Beatriz ;

Pastor, Isidro M. ;

Baeza, Alejandro .

ACS ORGANIC & INORGANIC AU, 2024, 4 (03) :269-286

[25] Asymmetric allylic alkylation using a palladium complex of chiral 2-(phosphinoaryl)pyridine ligands [J].

Ito, K ;

Kashiwagi, R ;

Iwasaki, K ;

Katsuki, T .

SYNLETT, 1999, (10) :1563-1566

[26] Palladium-catalyzed asymmetric allylic alkylation using chiral hydrazone ligands with ferrocene skeleton [J].

Mino, T ;

Segawa, H ;

Yamashita, M .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (17) :2833-2836

[27] Novel chiral phosphine-oxazinane ligands in palladium-catalyzed asymmetric allylic alkylation [J].

Mino, T ;

Hata, S ;

Ohtaka, K ;

Sakamoto, M ;

Fujita, T .

TETRAHEDRON LETTERS, 2001, 42 (29) :4837-4839

[28] Palladium-catalyzed asymmetric allylic alkylation of ketone enolates [J].

Trost, BM ;

Schroeder, GM .

CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (01) :174-184

[29] Versatile ligands for palladium-catalyzed asymmetric allylic alkylation [J].

Dierkes, P ;

Ramdeehul, S ;

Barloy, L ;

De Cian, A ;

Fischer, J ;

Kamer, PCJ ;

van Leeuwen, PWNM ;

Osborn, JA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1998, 37 (22) :3116-3118

[30] Stereoselective Three-Component Allylic Alkylation Enabled by Dual Photoredox/Ni Catalysis [J].

Zeng, Qian ;

Gao, Fengyun ;

Benet-Buchholz, Jordi ;

Kleij, Arjan W. .

ACS CATALYSIS, 2023, 13 (11) :7514-7522

← 1 2 3 4 5 →