Catalytic Asymmetric Synthesis of N-Chiral Amine Oxides

被引：22

作者：

Bhadra, Sukalyan ^{[1
,2
]}

Yamamoto, Hisashi ^{[1
]}

机构：

[1] Chubu Univ, Mol Catalyst Res Ctr, 1200 Matsumoto Cho, Kasugai, Aichi 4878501, Japan

[2] CSIR Cent Salt & Marine Chem Res Inst, Inorgan Mat & Catalysis Div, GB Marg, Bhavnagar 364002, Gujarat, India

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 42期

关键词：

asymmetric catalysis; dynamic kinetic resolution; homogeneous catalysis; nitrogen oxides; titanium; BETA-HYDROXY AMINES; KINETIC RESOLUTION; ALCOHOLS; SULFOXIDATION; EPOXIDATION; LIGAND;

D O I：

10.1002/anie.201606354

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Direct asymmetric synthesis of N-chiral amine oxides was accomplished (up to 91:9 e.r.) by means of a bimetallic titanium catalyst. A hydroxy group situated at the g-position of the N stereocenter enables the desired N-oxidation through dynamic kinetic resolution of the trivalent amine substrates. The method was further extended to the kinetic resolution of racemic g-amino alcohols with a preexisting stereocenter, giving an important class of enantioenriched (up to 99.9:0.1 e.r.) building blocks that are otherwise difficult to synthesize.

引用

页码：13043 / 13046

页数：4

共 50 条

[1] Synthesis, structure, and stereodynamics of an N,N-chiral "proton sponge"
Charmant, JPH
Lloyd-Jones, GC
Peakman, TM
Woodward, RL
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1999, 1999 (10) : 2501 - 2510
[2] A parallel preparation of a bicyclic N-chiral amine library and its use for chiral catalyst screening
Uozumi, Y
Mizutani, K
Nagai, S
TETRAHEDRON LETTERS, 2001, 42 (03) : 407 - 410
[3] Chiral tertiary amine N-oxides in asymmetric epoxidation of α,β-unsaturated ketones
Oh, Kyungsoo
Ryu, Jinhyang
TETRAHEDRON LETTERS, 2008, 49 (12) : 1935 - 1938
[4] Catalytic asymmetric epoxidation with a chiral ruthenium porphyrin and N-oxides
Berkessel, A
Frauenkron, M
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (16): : 2265 - 2266
[5] Recent Advances in Catalytic Asymmetric Synthesis of P-Chiral Phosphine Oxides
Zhu, Ren-Yi
Liao, Kui
Yu, Jin-Sheng
Zhou, Jian
ACTA CHIMICA SINICA, 2020, 78 (03) : 193 - 216
[6] Catalytic Asymmetric Hydrophosphinylation of α,β-Unsaturated N-Acylpyrroles: Application of Dialkyl Phosphine Oxides in Enantioselective Synthesis of Chiral Phosphine Oxides or Phosphines
Zhao, Depeng
Mao, Lijuan
Wang, Yuan
Yang, Dongxu
Zhang, Quanliang
Wang, Rui
ORGANIC LETTERS, 2010, 12 (08) : 1880 - 1882
[7] Synthesis and stereoselective dealkylation of N-chiral quarternary N-alkyl galanthaminium halides
Hirnschall, M
Treu, M
Mereiter, K
Hametner, C
Fröhlich, J
Jordis, U
TETRAHEDRON-ASYMMETRY, 2003, 14 (06) : 675 - 681
[8] Chiral N-acylhydrazones:: Versatile imino acceptors for asymmetric amine synthesis
Friestad, GK
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (15) : 3157 - 3172
[9] Chiral N-oxides in asymmetric catalysis
Malkov, Andrei V.
Kocovsky, Pavel
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (01) : 29 - 36
[10] Catalytic Asymmetric Synthesis of Chiral Benzofuranones
Li, Yao
Li, Xin
Cheng, Jin-Pei
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (06) : 1172 - 1198

← 1 2 3 4 5 →