Asymmetric catalytic [4+3] cycloaddition of ortho-quinone methides with oxiranes

被引：23

作者：

Tan, Qingfa ^{[1
]}

Yu, Han ^{[1
]}

Luo, Yao ^{[1
]}

Chang, Fenzhen ^{[1
]}

Liu, Xiaohua ^{[1
]}

Zhou, Yuqiao ^{[1
]}

Feng, Xiaoming ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Key Lab Green Chem & Technol, Minist Educ, Chengdu 610064, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2021年 / 57卷 / 24期

基金：

中国国家自然科学基金;

关键词：

BIOSYNTHESIS; ANNULATION; ALKALOIDS;

D O I：

10.1039/d1cc00262g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Catalytic enantioselective [4+3] cycloaddition reaction between o-quinone methides and oxiranes was achieved by using a chiral N,N '-dioxide/Tb-III complex as the catalyst, affording medium-sized hydrodioxepine derivatives in high yields (up to 99%) with good to excellent diastereo-(up to 94 : 6 dr) and enantioselectivities (up to 97% ee). The topographic steric maps and distribution of the buried volume (% V-Bur) of the catalysts via Cavallo's SambVca 2 tool were collected to effectively represent the chiral pocket of metal complexes of chiral N,N '-dioxides.

引用

页码：3018 / 3021

页数：4

共 50 条

[41] Base-mediated diastereoselective [4+3] annulation of in situ generated ortho-quinone methides with C, N-cyclic azomethine imines
Xu, Jianfeng
Yuan, Shiru
Peng, Jingyi
Miao, Maozhong
Chen, Zhengkai
Ren, Hongjun
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (36) : 7513 - 7517
[42] Chemoselective acid-catalyzed [4+2]-cycloaddition reactions of ortho-quinone methides and styrenes/stilbenes/cinnamates
Akkarasereenon, Kornkamon
Tangdenpaisal, Kassrin
Ruchirawat, Somsak
Ploypradith, Poonsakdi
ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (43) : 8854 - 8866
[43] Synthesis of 4H-chromenes by silver (I)-catalyzed cycloaddition of ortho-quinone methides with N-allenamides
Kong, Long
Thirupathi, Nuligonda
Jia, Jiong
Xu, Zhenghu
SCIENCE CHINA-CHEMISTRY, 2019, 62 (01) : 80 - 86
[44] Synthesis of 4H-chromenes by silver (I)-catalyzed cycloaddition of ortho-quinone methides with N-allenamides
Long Kong
Nuligonda Thirupathi
Jiong Jia
Zhenghu Xu
Science China Chemistry, 2019, 62 : 80 - 86
[45] Dearomative [4+2] Cycloaddition of Oxindole-Embedded ortho-Quinone Methides with 2,5-Dialkylfurans
Shen, Yao-Bin
Li, Shuai-Shuai
Liu, Xicheng
Yu, Liping
Liu, Qing
Xiao, Jian
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (06) : 1453 - 1458
[46] [4+2] cycloaddition of ortho-quinone methides promoted by ionic liquids:: an efficient and mild protocol for the synthesis of tetrahydropyranobenzopyrans
Yadav, JS
Reddy, BVS
Sadashiv, K
Padmavani, B
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (06) : 607 - 610
[47] 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
[48] Chemoselective oxidative generation of ortho-quinone methides and tandem transformations
Muhammet Uyanik
Kohei Nishioka
Ryutaro Kondo
Kazuaki Ishihara
Nature Chemistry, 2020, 12 : 353 - 362
[49] Defining the Synthetic Scope of ortho-Quinone Methides by Quantifying their Electrophilicity
Gross, Christoph
Eitzinger, Andreas
Hampel, Nathalie
Mayer, Peter
Ofial, Armin R.
Chemistry - A European Journal, 2024,
[50] Chiral Bronsted Acid-Catalyzed Asymmetric Reaction via Vinylidene Ortho-Quinone Methides
Zhu, Xin-Qi
Yang, Hai-Yu
Ye, Long-Wu
CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (49)

← 1 2 3 4 5 →