Lewis Acid Catalyzed [4+2] Cycloaddition of N-Tosylhydrazones with ortho-Quinone Methides

被引：23

作者：

Wang, Chun-Ying ^{[1
]}

Han, Jia-Bin ^{[1
]}

Wang, Long ^{[1
]}

Tang, Xiang-Ying ^{[1
]}

机构：

[1] Huazhong Univ Sci & Technol, Sch Chem & Chem Engn, Hubei Key Lab Bioinorgan Chem & Mat Med, Key Lab Mat Chem Energy Convers & Storage, 1037 Luoyu Rd, Wuhan 430074, Hubei, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 21期

基金：

中国国家自然科学基金;

关键词：

METAL-FREE SYNTHESIS; X-H X; TRANSITION-METAL; CONSTRUCTION; CYCLOPROPANATION; CYCLIZATION; ACTIVATION; ALKYLATION; PORPHYRIN; PYRAZOLES;

D O I：

10.1021/acs.joc.9b02040

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A formal [4 + 2] cycloaddition of N-tosylhydrazones with ortho-quinone methides was developed, affording the facile synthesis of diverse 1,3-oxazine derivatives under mild conditions. In this transformation, N-tosylhydrazones are used as a 1,2-dipole synthon under base-free conditions. Moreover, the substrate scope is broad, and the products are formed with high diastereoselectivities in most of the cases.

引用

页码：14258 / 14269

页数：12

共 50 条

[31] Catalytic Asymmetric [4+2] Cycloaddition of ortho-Alkenyl Naphthols/Phenols with ortho-Quinone Methides: Highly Stereoselective Synthesis of Chiral 2,3,4-Trisubstituted Chromans
Feng, Shubo
Yang, Binmiao
Chen, Tao
Wang, Ran
Deng, Yu-Hua
Shao, Zhihui
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (08): : 5231 - 5244
[32] Enantioselective Addition of Thiols to ortho-Quinone Methides Catalyzed by Chiral Phosphoric Acids
Lai, Zengwei
Sun, Jianwei
SYNLETT, 2016, 27 (04) : 555 - 558
[33] Enantioselective [4+1] cycloaddition of ortho-quinone methides and bromomalonates under phase-transfer catalysis
Lian, Xiao-Lei
Adili, Alafate
Liu, Bin
Tao, Zhong-Lin
Han, Zhi-Yong
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (17) : 3670 - 3673
[34] Direct Sulfide-Catalyzed Diastereoselective [4+1] Annulations of ortho-Quinone Methides and Bromides
Liu, Yan-Qing
Li, Qing-Zhu
Zhu, Hong-Ping
Feng, Xin
Peng, Cheng
Huang, Wei
Li, Jun-Long
Han, Bo
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (20): : 12753 - 12762
[35] Enantioselective Synthesis of Spiro Chroman-Isoindolinones via Formal (4+2) Cycloaddition of In Situ-Generated ortho-Quinone Methides with 3-Methylene Isoindolinones
Wang, Tao
Huang, Bo
Wang, You-Qing
ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (15) : 2596 - 2605
[36] Catalytic Asymmetric Dearomatization of 2,3-Disubstituted Indoles by a [4+2] Cycloaddition Reaction with In Situ Generated Vinylidene ortho-Quinone Methides: Access to Polycyclic Fused Indolines
Shikari, Amit
Parida, Chandrakanta
Pan, Subhas Chandra
ORGANIC LETTERS, 2024, 26 (24) : 5057 - 5062
[37] Scandium (III)-Catalyzed Cycloaddition of in situ Generated ortho-Quinone Methides with Vinyl Azides: An Efficient Access to Substituted 4H-Chromenes
Thirupathi, Nuligonda
Tung, Chen-Ho
Xu, Zhenghu
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (18) : 3585 - 3589
[38] Catalytic asymmetric [4+2] cycloaddition of 1-((2-aryl)vinyl)naphthalen-2-ols with in situ generated ortho-quinone methides for the synthesis of polysubstituted chromanes
You, Yong
Li, Ting-Ting
Yuan, Shu-Pei
Xie, Ke-Xin
Wang, Zhen-Hua
Zhao, Jian-Qiang
Zhou, Ming-Qiang
Yuan, Wei-Cheng
CHEMICAL COMMUNICATIONS, 2020, 56 (03) : 439 - 442
[39] Chiral Primary Amine Catalyzed Asymmetric α-Benzylation with In Situ Generated ortho-Quinone Methides
Zhu, Yunbo
Zhang, Wen-Zhao
Zhang, Long
Luo, Sanzhong
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (06) : 1253 - 1257
[40] Catalytic Asymmetric Cycloaddition of In Situ-Generated ortho-Quinone Methides and Azlactones by a Triple BrOnsted Acid Activation Strategy
Yu, Xiao-Ye
Chen, Jia-Rong
Wei, Qiang
Cheng, Hong-Gang
Liu, Zhi-Cheng
Xiao, Wen-Jing
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (20) : 6774 - 6778

← 1 2 3 4 5 →