Lewis-Acid-Catalyzed Tandem Cyclization by Ring Expansion of Tertiary Cycloalkanols with Propargyl Alcohols

被引：10

作者：

Li, Xue-Song ^{[1
]}

Kong, Xiangtao ^{[2
]}

Wang, Cui-Tian ^{[1
]}

Niu, Zhi-Jie ^{[1
]}

Wei, Wan-Xu ^{[1
]}

Liu, Hong-Chao ^{[1
]}

Zhang, Zhe ^{[1
]}

Li, Yuke ^{[3
,4
]}

Liang, Yong-Min ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[2] Anyang Normal Univ, Coll Chem & Chem Engn, Henan Key Lab New Optoelect Funct Mat, Anyang 455000, Peoples R China

[3] Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong 999077, Peoples R China

[4] Chinese Univ Hong Kong, Ctr Sci Modeling & Computat, Shatin, Hong Kong 999077, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 24期

基金：

中国国家自然科学基金;

关键词：

C BOND-CLEAVAGE; EFFICIENT SYNTHESIS; STRATEGY; CYCLOBUTANOLS; ANNULATION; ALKYNES; FUNCTIONALIZATION; ACTIVATION; ARYLATION; ACCESS;

D O I：

10.1021/acs.orglett.1c03621

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method for the efficient synthesis of hexahydro-1H-fluorene and octahydrobenzo[a]azulene derivatives through a ring-expansion strategy is reported. With an appropriate combination of thulium(III) trifluoromethanesulfonate and 13X molecular sieves, a range of unsaturated polycyclic compounds were obtained in good yields. Mechanism studies reveal that the reaction is more likely to undergo Meyer-Schuster rearrangement, ring expansion, and Friedel-Crafts-type pathways, which provide a conceptually different strategy for the ring opening of tertiary cycloalkanols.

引用

页码：9457 / 9462

页数：6

共 50 条

[41] Lewis Acid Catalyzed Domino Ring-Opening Cyclization of Azetidines with Alkynes: Synthesis of Tetrahydropyridines
Shukla, Dipti
Singh, Shishir
Sharma, Amit Kumar
Singh, Bharat
Bhattacharyya, Aditya
Talukdar, Ranadeep
Ghorai, Manas K.
SYNLETT, 2024, 35 (20) : 2459 - 2464
[42] Silver-Catalyzed Carboxylative Cyclization of Primary Propargyl Alcohols with CO2
Dabral, Saumya
Bayarmagnai, Bilguun
Hermsen, Marko
Schiessl, Jasmin
Mormul, Verena
Hashmi, A. Stephen K.
Schaub, Thomas
ORGANIC LETTERS, 2019, 21 (05) : 1422 - 1425
[43] Lewis acid-catalyzed nucleophilic ring-opening/intramolecular Conia-ene reactions of methylenecyclopropane 1,1-diesters with propargyl alcohols
Hu, Bao
Ren, Jun
Wang, Zhongwen
TETRAHEDRON, 2011, 67 (04) : 763 - 768
[44] Ruthenium(II)-Catalyzed Regioselective-Controlled Allenylation/Cyclization of Benzimides with Propargyl Alcohols
Anukumar, Adapa
Tamizmani, Masilamani
Jeganmohan, Masilamani
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (15): : 8567 - 8580
[45] INTERNAL LEWIS ACID-CATALYZED RING-EXPANSION REACTIONS OF CYCLOPROPYLALKANOYL CHLORIDES
DOYLE, MP
BADE, TR
TETRAHEDRON LETTERS, 1975, (35) : 3031 - 3034
[46] Construction of Benzopolycycles via Pd-Catalyzed Intermolecular Cyclization of 2,7-Alkadiynylic Carbonates with Terminal Propargyl Tertiary Alcohols
Zhang, Yuchen
Fu, Chunling
Huang, Xin
Ma, Shengming
ORGANIC LETTERS, 2019, 21 (10) : 3523 - 3527
[47] Desymmetrizing Asymmetric Ring Expansion of Cyclohexanones with α-Diazoacetates Catalyzed by Chiral Aluminum Lewis Acid
Hashimoto, Takuya
Naganawa, Yuki
Maruoka, Keiji
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (23) : 8834 - 8837
[48] Enantioselective PhSe-group-transfer tandem radical cyclization reactions catalyzed by a chiral Lewis acid
Yang, D
Zheng, BF
Gao, Q
Gu, S
Zhu, NY
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (02) : 255 - 258
[49] Mild boronic acid catalyzed Nazarov cyclization of divinyl alcohols in tandem with Diels-Alder cycloaddition
Zheng, Hongchao
Lejkowski, Michal
Hall, Dennis G.
TETRAHEDRON LETTERS, 2013, 54 (01) : 91 - 94
[50] Effect of Substituent on the Mechanism and Chemoselectivity of the Gold(I)-Catalyzed Propargyl Ester Tandem Cyclization
Li, Yunhe
Kirillov, Alexander M.
Fang, Ran
Yang, Lizi
ORGANOMETALLICS, 2017, 36 (06) : 1164 - 1172

← 1 2 3 4 5 →