Catalytic Diastereospecific and Enantioselective (3+2) Transannulations of 1,2,3-Thiadiazoles with Strained Norbornene Derivatives

被引：17

作者：

Chen, Cunzhi ^{[1
]}

Fang, Shuyan ^{[1
]}

Dong, Ziyang ^{[1
]}

Xu, Jiaxi ^{[1
]}

Yang, Zhanhui ^{[1
]}

机构：

[1] Beijing Univ Chem Technol, Coll Chem, Dept Organ Chem, Beijing 100029, Peoples R China

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 11期

基金：

中国国家自然科学基金;

关键词：

CARBENES; ENERGIES;

D O I：

10.1021/acs.orglett.2c00330

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

With the adoption of a ring-strain-release strategy, iridium-catalyzed transannulations with norbornene derivatives are achieved in a diastereospecific and enantioselective manner. The first asymmetric transannulations of 1,2,3-thiadiazoles are reported.

引用

页码：2110 / 2114

页数：5

共 24 条

[1] Gold-catalyzed heterocyclic syntheses through α-imino gold carbene complexes as intermediates Dedicated to Professor Dr Julius Rebek, Jr. on the occasion of his 75th birthday. [J].

Aguilar, Enrique ;

Santamaria, Javier .

ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (09) :1513-1540

[2] The effect of substitutents on the strain energies of small ring compounds [J].

Bach, RD ;

Dmitrenko, O .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (08) :2588-2599

[3] Palladium-Catalyzed Intermolecular Alkene Carboacylation via Ester C-O Bond Activation [J].

Banovetz, Haley K. ;

Vickerman, Kevin L. ;

David, Colton M. ;

Alkan, Melisa ;

Stanley, Levi M. .

ORGANIC LETTERS, 2021, 23 (09) :3507-3512

[4] Dual roles of bisphosphines and epoxides: Rh-catalyzed highly chemoselective and diastereoselective (3+2) transannulations of 1,2,3-thiadiazoles with cyanoepoxides [J].

Dong, Ziyang ;

Chen, Cunzhi ;

Wang, Jing ;

Xu, Jiaxi ;

Yang, Zhanhui .

ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (23) :6687-6698

[5] Modern Organic Synthesis with α-Diazocarbonyl Compounds [J].

Ford, Alan ;

Miel, Hugues ;

Ring, Aoife ;

Slattery, Catherine N. ;

Maguire, Anita R. ;

McKervey, M. Anthony .

CHEMICAL REVIEWS, 2015, 115 (18) :9981-10080

[6] Ring strain energies: substituted rings, norbornanes, norbornenes and norbornadienes [J].

Khoury, PR ;

Goddard, JD ;

Tam, W .

TETRAHEDRON, 2004, 60 (37) :8103-8112

[7] Rhodium-Catalyzed Intramolecular Transannulation Reaction of Alkynyl Thiadiazole Enabled 5,n-Fused Thiophenes [J].

Kim, Ji Eun ;

Lee, Jinsub ;

Yun, Hyunsik ;

Baek, Yonghyeon ;

Lee, Phil Ho .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (03) :1437-1447

[8] Rhodium Thiavinyl Carbenes from 1,2,3-Thiadiazoles Enable Modular Synthesis of Multisubstituted Thiophenes [J].

Kurandina, Dania ;

Gevorgyan, Vladimir .

ORGANIC LETTERS, 2016, 18 (08) :1804-1807

[9] Rhodium-Catalyzed Cyclization Reactions of Thiadiazoles with Phosphaalkynes to Prepare 1,3-Thiaphospholes [J].

Liang Wenbin ;

Nakajima, Kazunari ;

Nishibayashi, Yoshiaki .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (25) :3879-3882

[10] Mechanistic insights into the Rh(i)-catalyzed transannulation of 1,2,3-thiadiazoles with alkenes, alkynes, and nitriles: Does the intermediacy of α-thiavinyl Rh-carbenoids play an important role? [J].

Lv, Kang ;

Bao, Xiaoguang .

ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (02) :310-318

← 1 2 3 →