Nickel-catalyzed ring-opening of α-hydroxycyclobutenones with a remarkable ligand effect

被引:8
作者
Gao, Songsong [1 ]
Hu, Xiangdong [1 ]
机构
[1] Northwest Univ, Minist Educ China, Key Lab Synthet & Nat Funct Mol Chem, Sch Chem & Mat Sci, Xian 710127, Shaanxi, Peoples R China
基金
中国国家自然科学基金; 中国博士后科学基金;
关键词
C-C BOND; CONROTATORY ELECTROCYCLIC REACTIONS; CYCLOBUTENONE REARRANGEMENTS; STEREOSELECTIVE-SYNTHESIS; INWARD TORQUOSELECTIVITY; ORGANIC-SYNTHESIS; TETRONIC ACIDS; PULVINIC ACID; LEWIS-ACID; SUBSTITUENT;
D O I
10.1039/c7cc03340k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A Ni-catalyzed ring-opening of alpha-hydroxycyclobutenones is reported herein. A remarkable ligand effect was observed during transformations following the ring-opening. The employment of PPh3 leads to the formation of 2-furanones 2 through a migration of an alkoxyl group, and 2-furanones 3 were generated through a migration of hydrogen in the presence of Xantphos, affording a divergent approach to 2-furanones bearing multiple functional groups.
引用
收藏
页码:10540 / 10543
页数:4
相关论文
共 81 条
[1]   DFT study of pericyclic reaction cascades in the synthesis of antibiotic TAN-1085 [J].
Akerling, ZR ;
Norton, JE ;
Houk, KN .
ORGANIC LETTERS, 2004, 6 (23) :4273-4275
[2]   Total Synthesis of Carbazomycin G by a Thermal Ring Expansion/Self-Redox Reaction Cascade [J].
An, Yong ;
Wang, Yunxia ;
Hu, Xiangdong .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (17) :3715-3718
[3]  
[Anonymous], ANGEW CHEM
[4]   Cyclobutenones and Benzocyclobutenones: Versatile Synthons in Organic Synthesis [J].
Chen, Peng-hao ;
Dong, Guangbin .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (51) :18290-18315
[5]   TOTAL SYNTHESIS OF MYCOPHENOLIC-ACID [J].
DANHEISER, RL ;
GEE, SK ;
PEREZ, JJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (04) :806-810
[6]   New annulation reactions of cyclobutenones [J].
Dillon, JL ;
Gao, Q ;
Dillon, EA ;
Adams, N .
TETRAHEDRON LETTERS, 1997, 38 (13) :2231-2234
[7]   Electronic control of stereoselectivities of electrocyclic reactions of cyclobutenes: A triumph of theory in the prediction of organic reactions [J].
Dolbier, WR ;
Koroniak, H ;
Houk, KN ;
Sheu, CM .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (10) :471-477
[8]   KINETIC AND THERMODYNAMIC EFFECTS IN THE THERMAL ELECTROCYCLIC RING-OPENINGS OF 3-FLUOROCYCLOBUTENE, 3,3-DIFLUOROCYCLOBUTENE, AND 3-(TRIFLUOROMETHYL)CYCLOBUTENE [J].
DOLBIER, WR ;
GRAY, TA ;
KEAFFABER, JJ ;
CELEWICZ, L ;
KORONIAK, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (01) :363-367
[9]   CONSTITUENTS OF HIGHER FUNGI .12. IDENTIFICATION OF INVOLUTIN AS (-)-CIS-5-(3,4-DIHYDROXYPHENYL)-3,4-DIHYDROXY-2-(4-HYDROXYPHENYL)-CYCLOPENT-2-ENONE AND SYNTHESIS OF (+/-)-CIS-INVOLUTIN TRIMETHYL ETHER FROM ISOXEROCOMIC ACID DERIVATIVES [J].
EDWARDS, RL ;
GILL, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (15) :1529-1537
[10]   Enantioselective preparation of 1-hydroxy neoisopulegol and 1-hydroxy neoisomenthol [J].
Fkyerat, A ;
Tabacchi, R .
TETRAHEDRON-ASYMMETRY, 1997, 8 (13) :2231-2236