Organocatalytic Asymmetric Construction of Tetrasubstituted Carbon Stereocenters Bearing Three Heteroatoms via Intramolecular Cyclization of Vinylidene ortho-Quinone Methide with Imidates

被引：6

作者：

Tian, Yuhong ^{[1
]}

Wu, Fengdi ^{[1
]}

Jia, Shiqi ^{[1
]}

Gong, Xiangnan ^{[2
]}

Mao, Hui ^{[3
]}

Wang, Pengfei ^{[1
]}

Qin, Wenling ^{[1
]}

Yan, Hailong ^{[1
]}

机构：

[1] Chongqing Univ, Sch Pharmaceut Sci, Chongqing Key Lab Nat Prod Synth & Drug Res, Chongqing 401331, Peoples R China

[2] Chongqing Univ, Analyt & Testing Ctr Chongqing Univ, Chongqing 401331, Peoples R China

[3] Jinhua Polytech, Coll Pharm, Jinhua 321007, Zhejiang, Peoples R China

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 28期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE CONSTRUCTION; BOND;

D O I：

10.1021/acs.orglett.2c01842

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report herein an organocatalytic asymmetric protocol for the construction of tetrasubstituted carbon stereocenters bearing three heteroatoms. The reaction proceeded via the enantioselective intramolecular cyclization reaction of vinylidene ortho-quinone methide (VQM) with imidates to form pentacyclic heterocycles. The formed tetrasubstituted carbon center was stable under a high temperature and the conditions for further transformations.

引用

页码：5073 / 5077

页数：5

共 4 条

[1] Mechanistic Features of Asymmetric Vinylidene ortho-Quinone Methide Construction and Subsequent Transformations
Xu, Da
Chang, Yu
Liu, Yidong
Qin, Wenling
Yan, Hailong
ACS CATALYSIS, 2023, 13 (05) : 2957 - 2967
[2] Asymmetric synthesis of chromene skeletons via organocatalytic domino reactions of in situ generated ortho-quinone methide with malononitrile and β-functionalized ketone
Zhang, Lili
Zhou, Xiao
Li, Pengfei
Liu, Zhantao
Liu, Yang
Sun, Yong
Li, Wenjun
RSC ADVANCES, 2017, 7 (62) : 39216 - 39220
[3] N-Iodosuccinimide-Mediated Dimerization of 2-Alkynylnaphthols: A Highly Diastereoselective Construction of Bridged Polycyclic Compounds via Vinylidene ortho-Quinone Methide Intermediate
Tan, Yu
Zhao, Zhengxing
Chen, Zhili
Huang, Shengli
Jia, Shiqi
Peng, Lei
Xu, Da
Qin, Wenling
Yan, Hailong
ORGANIC LETTERS, 2020, 22 (11) : 4461 - 4466
[4] SYNTHESIS Best Paper Award 2022: Asymmetric Synthesis of Fused Tetrahydroquinolines via Intramolecular Aza-Diels-Alder Reaction of ortho-Quinone Methide Imines
Zanda, Matteo
Kretzschmar, M.
Schneider, C.
Synthesis (Germany), 2023, 55 (07):

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