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

[41] Cooperative Catalysis by Palladium and a Chiral Phosphoric Acid: Enantioselective Amination of Racemic Allylic Alcohols
Banerjee, Debasis
Junge, Kathrin
Beller, Matthias
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (48) : 13049 - 13053
[42] PALLADIUM CATALYSIS AS A MEANS FOR PROMOTING THE ALLYLIC C-ALKYLATION OF NITRO-COMPOUNDS
WADE, PA
MORROW, SD
HARDINGER, SA
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (02): : 365 - 367
[43] Palladium-Catalyzed Allylic Alkylation of Simple Ketones with Allylic Alcohols and Its Mechanistic Study
Huo, Xiaohong
Yang, Guoqiang
Liu, Delong
Liu, Yangang
Gridnev, Ilya D.
Zhang, Wanbin
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (26) : 6776 - 6780
[44] ASYMMETRIC INDUCTION IN ALLYLIC REARRANGEMENT OF CHIRAL AMINE OXIDE
YAMAMOTO, Y
ODA, J
INOUYE, Y
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (22) : 848 - 849
[45] Recent Advances on the Catalytic Asymmetric Allylic α-Alkylation of Carbonyl Derivatives Using Free Allylic Alcohols
Alonso, Diego A.
Macia, Beatriz
Pastor, Isidro M.
Baeza, Alejandro
ACS ORGANIC & INORGANIC AU, 2024, 4 (03): : 269 - 286
[46] Palladium-Catalyzed Allylic Alkylation Reactions of Nucleophilic Allenones: Asymmetric Allylic Alkylation, Z/E Divergent Allylic Alkylation, and [5+2] Annulation
Wang, Wang
Hu, Yimin
Li, Kuan
Xu, Jiaqing
Zhang, Cheng
Zhou, Leijie
Zhu, Lihan
Guo, Hongchao
ACS CATALYSIS, 2024, 14 (13): : 9940 - 9954
[47] Development of proline derived chiral aminophosphine ligands for palladium-catalyzed asymmetric allylic alkylation
Mino, Takashi
Tanaka, Youichi
Sakamoto, Masami
Fujita, Tsutomu
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2006, 64 (06) : 628 - 638
[48] Palladium-catalyzed asymmetric allylic alkylation using chiral pyridyl-hydrazone ligands
Mino, Takashi
Shirae, Yoshiaki
Yajima, Torn
Sakamoto, Masami
Fujita, Tsutomu
HETEROCYCLES, 2006, 68 (06) : 1233 - +
[49] Palladium-catalyzed asymmetric allylic alkylation using chiral glucosamine-based monophosphines
Tollabi, M
Framery, E
Goux-Henry, C
Sinou, D
TETRAHEDRON-ASYMMETRY, 2003, 14 (21) : 3329 - 3333
[50] Asymmetric allylic alkylation using a palladium complex of chiral 2-(phosphinoaryl)pyridine ligands
Ito, K
Kashiwagi, R
Iwasaki, K
Katsuki, T
SYNLETT, 1999, (10) : 1563 - 1566

← 1 2 3 4 5 →