Asymmetric dearomatization of benzyl 1-naphthyl ethers via [1,3] O-to-C rearrangement

被引：1

作者：

Zeng, Hongkun ^{[1
]}

Wen, Gang ^{[1
]}

Lin, Lili ^{[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 | 2024年 / 60卷 / 58期

关键词：

CLAISEN REARRANGEMENT; OXINDOLES; PHENOLS;

D O I：

10.1039/d4cc02620a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A catalytic asymmetric dearomatization reaction of benzyl 1-naphthyl ethers accelerated by a chiral N,N '-dioxide/Co(ii) complex is disclosed. The reaction proceeds via an enantioselective [1,3] O-to-C rearrangement through a tight ion-pair pathway, providing a wide array of alpha-naphthalenone derivatives bearing an all-carbon quaternary center in high yields with excellent ee values.

引用

页码：7507 / 7510

页数：4

共 50 条

[31] Hydrogen bonding and C-H•••O interactions in 2-[1-(1-naphthyl)ethyl]benzoic acid at 150 K
Gerkin, RE
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2000, 56 (10): : 1222 - 1224
[32] Improved practical asymmetric synthesis of α-alkylmandelic acids utilizing highly diastereoselective alkylation of 5-aryl-2-(1-naphthyl)-1,3-dioxolan-4-ones
Misaki, Tomonori
Ureshino, Satoko
Nagase, Ryohei
Oguni, Yumiko
Tanabe, Yoo
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2006, 10 (03) : 500 - 504
[33] Formal [1,3] rearrangement of 2-furylmethyl and 2-thienylmethyl vinyl ethers
Palani, N
Balasubramanian, KK
TETRAHEDRON LETTERS, 1995, 36 (52) : 9527 - 9530
[34] An Unexpected Thermal [1,3]-[1,3]-para Rearrangement of Chromone-3-ylmethyl Aryl Ethers: Mechanism and Application of the Intercepted [1,3]-Rearranged Intermediates to the Synthesis of cis-Homopterocarpans
Devarajan, Krishnan
Devaraj, Somasundaram
Balasubramanian, Kalpattu K.
Bhagavathy, Shanmugasundaram
CHEMISTRY LETTERS, 2015, 44 (04) : 551 - 553
[35] 2,4-diamino-5-(1-naphthyl)-3,5-diaza-1-azoniaspiro[5.5]undeca-1,3-diene chloride
Papandreou, NC
Makedonopoulou, S
Antoniadou-Vyza, EA
Mavridis, IM
Hamodrakas, SJ
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 2002, 58 : O730 - O732
[36] (E)-2-[2-(1-Naphthyl)vinyl]-3-tosyl-2,3-dihydro-1,3-benzothiazole
Maiti, S
Mukherjee, M
Nandi, B
Helliwell, M
Kundu, NG
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2000, 56 : 992 - 994
[37] [1,2]- or [2,3]-rearrangement of onium ylides of allyl and benzyl ethers and sulfides via in situ-generated iodonium ylides
Murphy, Graham K.
West, F. G.
ORGANIC LETTERS, 2006, 8 (19) : 4359 - 4361
[38] Synthesis of o-hydroxyphenyl-alkoxymethylsilanes via [1,3]-(O->C)-silyl migration
Nietzschmann, E
Mrestani, Y
Liebau, M
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1996, 116 : 65 - 76
[39] Asymmetric synthesis of (S)-2-amino-3-(1-naphthyl)propanoic acid via chiral nickel complex.: Crystal structure, circular dichroism, 1H and 13C NMR spectra of the complex
Popkov, A
Císarová, I
Sopková, J
Jirman, J
Lycka, A
Kochetkov, KA
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2005, 70 (09) : 1397 - 1410
[40] 1,3-methoxy rearrangement of masked o-benzoquinones:: A novel synthesis of p-quinol ethers
Yang, Ching-Shun
Liao, Chun-Chen
ORGANIC LETTERS, 2007, 9 (23) : 4809 - 4812

← 1 2 3 4 5 →