Tandem Insertion-[1,3]-Rearrangement: Highly Enantioselective Construction of α-Aminoketones

被引：49

作者：

Chen, Yushuang ^{[1
]}

Liu, Yun ^{[1
]}

Li, Zhaojing ^{[1
]}

Dong, Shunxi ^{[1
]}

Liu, Xiaohua ^{[1
]}

Feng, Xiaoming ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Key Lab Green Chem & Technol, Minist Educ, Chengdu 610064, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2020年 / 59卷 / 21期

基金：

中国国家自然科学基金;

关键词：

1,3]-rearrangement; asymmetric synthesis; bimetallic catalysis; tandem reaction; alpha-aminoketone; TO-C REARRANGEMENT; CLAISEN REARRANGEMENT; 1,3 O; ASYMMETRIC-SYNTHESIS; MIGRATION REACTIONS; RELAY CATALYSIS; AMINO KETONES; ALCOHOLS; ROUTE; BONDS;

D O I：

10.1002/anie.201914645

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An enantioselective synthesis of alpha-aminoketone derivatives were readily available through a tandem insertion[1,3] O-to-C rearrangement reaction. The rhodium salt and chiral N,N'-dioxide-indium(III) complex make up relay catalysis, which enables the O-H insertion of benzylic alcohols to N-sulfonyl-1,2,3-triazoles, and asymmetric [1,3]-rearrangement of amino enol ether intermediates, subsequently. Preliminary mechanistic studies suggested that the [1,3] O-to-C rearrangement step proceeded through an ion pair pathway.

引用

页码：8052 / 8056

页数：5

共 93 条

[41] Asymmetric Cycloaddition and Cyclization Reactions Catalyzed by Chiral N,N′-Dioxide-Metal Complexes [J].

Liu, Xiaohua ;

Zheng, Haifeng ;

Xia, Yong ;

Lin, Lili ;

Feng, Xiaoming .

ACCOUNTS OF CHEMICAL RESEARCH, 2017, 50 (10) :2621-2631

[42] Chiral N,N′-dioxide ligands: synthesis, coordination chemistry and asymmetric catalysis [J].

Liu, Xiaohua ;

Lin, Lili ;

Feng, Xiaoming .

ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (03) :298-302

[43] Chiral N,N′-Dioxides: New Ligands and Organocatalysts for Catalytic Asymmetric Reactions [J].

Liu, Xiaohua ;

Lin, Lili ;

Feng, Xiaoming .

ACCOUNTS OF CHEMICAL RESEARCH, 2011, 44 (08) :574-587

[44] Ion pairing [J].

Marcus, Yizhak ;

Hefter, Glenn .

CHEMICAL REVIEWS, 2006, 106 (11) :4585-4621

[45] O→C rearrangements:: a powerful strategy for the synthesis of functionalised carbocycles [J].

Meek, Simon J. ;

Harrity, Joseph P. A. .

TETRAHEDRON, 2007, 63 (15) :3081-3092

[46] 1-(4-methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors [J].

Meltzer, PC ;

Butler, D ;

Deschamps, JR ;

Madras, BK .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (04) :1420-1432

[47] Tandem O-H Insertion/[3,3]-Sigmatropic Rearrangement of Rhodium Carbenoids with 2-Furfuryl Alcohols: A Strategy To Access Polysubstituted Furans [J].

Mi, Pengbing ;

Wang, Hannan ;

Zhao, Rui ;

Song, Jinna .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (06) :759-762

[48] Tandem O-H Insertion/[1,3]-Alkyl Shift of Rhodium Azavinyl Carbenoids with Benzylic Alcohols: A Route To Convert C-OH Bonds into C-C Bonds [J].

Mi, Pengbing ;

Kumar, Rapolu Kiran ;

Liao, Peiqiu ;

Bi, Xihe .

ORGANIC LETTERS, 2016, 18 (19) :4998-5001

[49]

Miura T., 2013, ANGEW CHEM, V125, P3975

[50] Synthesis of 2-Substituted 2-Amino Ketones by Rhodium-Catalyzed Reaction of N-Sulfonyl-1,2,3-triazoles with 2-Alkenols [J].

Miura, Tomoya ;

Tanaka, Takamasa ;

Zhao, Qiang ;

Stewart, Scott G. ;

Murakami, Masahiro .

HELVETICA CHIMICA ACTA, 2017, 100 (02)

← 1 2 3 4 5 6 7 8 9 10 →