Allylic C-H Amination for the Preparation of syn-1,3-Amino Alcohol Motifs

被引：196

作者：

Rice, Grant T. ^{[1
]}

White, M. Christina ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 33期

关键词：

ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; BETA-AMINO; HYDROCARBON OXIDATION; MANNICH REACTIONS; ENOL ETHERS; DERIVATIVES; CYCLIZATION; CATALYSIS; INSERTION;

D O I：

10.1021/ja9054959

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly selective and general Pd/sulfoxide-catalyzed allylic C-H amination reaction en route to syn-1,3-amino alcohol motifs is reported. Key to achieving this reactivity under mild conditions is the use of electron-deficient N-nosyl carbamate nucleophiles that are thought to promote functionalization by furnishing higher concentrations of anionic species in situ. The reaction is shown to be orthogonal to classical C-C bond-forming/-reduction sequences as well as nitrene-based C-H amination methods.

引用

页码：11707 / 11711

页数：5

共 35 条

[1] Pd(II)-Catalyzed Allylic C-H Amination for the Preparation of 1,2-and 1,3-Cyclic Ureas
Nishikawa, Yasuhiro
Kimura, Seikou
Kato, Yuri
Yamazaki, Natsuka
Hara, Osamu
ORGANIC LETTERS, 2015, 17 (04) : 888 - 891
[2] O2-Assisted Four-Component Reaction of Vinyl Magnesium Bromide with Chiral N-tert-Butanesulfinyl Imines To Form syn-1,3-Amino Alcohols
Wang, Runping
Luo, Jingfan
Zheng, Chunmei
Zhang, Hongyun
Gao, Lu
Song, Zhenlei
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (46) : 24644 - 24649
[3] TEMPO-mediated allylic C-H amination with hydrazones
Zhu, Xu
Chiba, Shunsuke
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (26) : 4567 - 4570
[4] Iron-Catalyzed Intramolecular Allylic C-H Amination
Paradine, Shauna M.
White, M. Christina
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (04) : 2036 - 2039
[5] A Catalytic, Bronsted Base Strategy for Intermolecular Allylic C-H Amination
Reed, Sean A.
Mazzotti, Anthony R.
White, M. Christina
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (33) : 11701 - 11706
[6] C-H Functionalization and Allylic Amination for Post-Polymerization Modification of Polynorbornenes
Gitter, Sean R.
Teh, Wei Pin
Yang, Xuejin
Dohoda, Alexander F.
Michael, Forrest E.
Boydston, Andrew J.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (23)
[7] α'-Selective Selenium-catalyzed Allylic C-H Amination of Enol Derivatives
Dohoda, Alexander F.
Rishwain, Nicole
Tran, Y-Nhi
Michael, Forrest E.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (40)
[8] Enantioselective Synthesis of Chiral Isoindolines via Palladium-Catalyzed Asymmetric Allylic C-H Amination
Chen, Yupeng
Jin, Yangbin
Li, Mingda
Li, Jiarui
Wu, Wanqing
Jiang, Huanfeng
CCS CHEMISTRY, 2024, : 973 - 981
[9] Anti-Markovnikov rearrangement in sulfur mediated allylic C-H amination of olefins
Zhang, Zhong
Du, Hongguang
Xu, Jiaxi
Li, Pingfan
CHEMICAL COMMUNICATIONS, 2016, 52 (77) : 11547 - 11550
[10] Metal-Free Allylic C-H Amination of Vinylsilanes and Vinylboronates using Silicon or Boron as a Regioselectivity Switch
Maloney, T. Parker
Berman, Janna L.
Michael, Forrest E.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (45)

← 1 2 3 4 →