Chiral Bronsted Acid-Catalyzed Kinetic Resolution of Sulfoximines for the Synthesis of Benzothiadiazine-1-Oxides

被引：1

作者：

Chen, Yuhang ^{[1
]}

Huang, Shihao ^{[1
]}

Wang, Tianyi ^{[1
]}

Li, Jiaomeng ^{[1
]}

Zhao, Yi ^{[1
]}

Zhou, Qinglong ^{[1
]}

Wei, Liwen ^{[1
]}

Yang, Xing ^{[1
]}

机构：

[1] Hunan Normal Univ, Coll Chem & Chem Engn, Key Lab Assembly & Applicat Organ Funct Mol Hunan, Key Lab Chem Biol & Tradit Chinese Med,Minist Educ, Changsha 410081, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 11期

基金：

中国国家自然科学基金;

关键词：

Amination; -; Amines; Scaffolds; Stereochemistry;

D O I：

10.1021/acs.joc.4c00623

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzothiadiazine-1-oxide scaffolds with S-stereogenic centers are prevalent in bioactive and pharmaceutical molecules. Reported works mainly focused on the metal-catalyzed asymmetric C-H amination/cyclization reaction for the synthesis of benzothiadiazine-1-oxides. Here, we reported a chiral phosphoric acid-catalyzed kinetic resolution of sulfoximines, providing chiral benzothiadiazine-1-oxides and recovered chiral sulfoximines with moderate to good enantioselectivities (s factors up to 36.6).

引用

页码：7970 / 7981

页数：12

共 50 条

[31] Chiral Bronsted acid-catalyzed asymmetric aza Diels-Alder reactions
Akiyama, Takahiko
Itoh, Junji
Fuchibe, Kohei
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
[32] Chiral Bronsted acid-catalyzed direct Mannich reactions via electrophilic activation
Uraguchi, D
Terada, M
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (17) : 5356 - 5357
[33] Recent Developments in the Chiral BrOnsted Acid-catalyzed Allylboration Reaction with Polyfunctionalized Substrates
Barrio, Pablo
Rodriguez, Elsa
Fustero, Santos
CHEMICAL RECORD, 2016, 16 (04): : 2046 - 2060
[34] Chiral Phosphoric Acid-Catalyzed Hydrolytic Parallel Kinetic Resolution of Racemic Epoxides and Activated Alcohols
Du, Yi-Ying
He, Yu-Shi
Liang, Yan
Liu, Xue-Song
Liu, Juan
Gai, Long-Hui
Liu, Shang-Zhong
Cao, Yi-Ming
ORGANIC LETTERS, 2025, 27 (08) : 1786 - 1791
[35] Chiral Phosphoric Acid-Catalyzed Oxidative Kinetic Resolution of Indolines Based on Transfer Hydrogenation to Imines
Saito, Kodai
Shibata, Yukihiro
Yamanaka, Masahiro
Akiyama, Takahiko
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (32) : 11740 - 11743
[36] DFT Study on Bifunctional Chiral Bronsted Acid-Catalyzed Asymmetric Hydrophosphonylation of Imines
Yamanaka, Masahiro
Hirata, Takashi
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (09): : 3266 - 3271
[37] Chiral Bronsted Acid-Catalyzed Enantioselective Three-Component Povarov Reaction
Liu, Hua
Dagousset, Guillaume
Masson, Geraldine
Retailleau, Pascal
Zhu, Jieping
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (13) : 4598 - +
[38] Asymmetric Bronsted acid catalyzed isoindoline synthesis: Enhancement of enantiomeric ratio by stereoablative kinetic resolution
Enders, Dieter
Narine, Arun A.
Toulgoat, Fabien
Bisschops, Tom
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (30) : 5661 - 5665
[39] Kinetic Resolution of Azomethine Imines by Bronsted Acid Catalyzed Enantioselective Reduction
Bongers, Amanda
Moon, Patrick J.
Beauchemin, Andre M.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (51) : 15516 - 15519
[40] Chiral Bronsted acid-catalyzed regio- and enantioselective arylation of α,β-unsaturated trifluoromethyl ketones
Pei, Zeng-kai
Zheng, Yan
Nie, Jing
Ma, Jun-An
TETRAHEDRON LETTERS, 2010, 51 (35) : 4658 - 4661

← 1 2 3 4 5 →