Ruthenium-catalyzed cycloaddition of propargylic alcohols with phenol derivatives via allenylidene intermediates:: Catalytic use of the allenylidene ligand as the C3 unit

被引:139
作者
Nishibayashi, Y
Inada, Y
Hidai, M
Uemura, S
机构
[1] Kyoto Univ, Dept Energy & Hydrocarbon Chem, Sakyo Ku, Kyoto 6068501, Japan
[2] Tokyo Univ Sci, Dept Mat Sci & Technol, Noda, Chiba 2788510, Japan
关键词
D O I
10.1021/ja026168x
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Novel ruthenium-catalyzed cycloaddition of propargylic alcohols with 2-naphthols and phenols bearing electron-donating groups via allenylidene intermediates has been developed to give the corresponding 1H-naphtho[2,1-b]pyrans and 4H-1-benzopyrans, respectively, in moderate to excellent yields with complete regioselectivity. Copyright © 2002 American Chemical Society.
引用
收藏
页码:7900 / 7901
页数:2
相关论文
共 35 条
[11]   Conical intersection mechanism for photochemical ring opening in benzospiropyran compounds [J].
Celani, P ;
Bernardi, F ;
Olivucci, M ;
Robb, MA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (44) :10815-10820
[12]   Synthesis of 2-alkoxy-5-methylenetetrahydropyrans: A regioselective ruthenium-catalyzed C-C coupling reaction of prop-2-yn-1-ols with allyl alcohol [J].
Derien, S ;
Ropartz, L ;
Le Paih, J ;
Dixneuf, PH .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3524-3531
[13]   1,2,3-diheterocyclization reactions on the allenylidene ligand of a ruthenium complex [J].
Esteruelas, MA ;
Gomez, AV ;
Lopez, AM ;
Onate, E .
ORGANOMETALLICS, 1998, 17 (16) :3567-3573
[14]   Addition of carbon nucleophiles to the allenylidene ligand of [Ru(η5-C5H5)(C=C=CPh2)(CO)(PiPr3)]BF4:: Synthesis of new organic ligands by formal C-C coupling between mutually inert fragments [J].
Esteruelas, MA ;
Gomez, AV ;
Lopez, AM ;
Modrego, J ;
Onate, E .
ORGANOMETALLICS, 1997, 16 (26) :5826-5835
[15]  
Fürstner A, 2000, CHEM-EUR J, V6, P1847
[16]   The first co-ordinatively unsaturated Group 8 allenylidene complexes:: insights into Grubbs' vs. Dixneuf-Furstner olefin metathesis catalysts [J].
Harlow, KJ ;
Hill, AF ;
Wilton-Ely, JDET .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1999, (03) :285-291
[17]   (p-cymene)RuLCl2 (L=1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene and 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) and related complexes as ring closing metathesis catalysts [J].
Jafarpour, L ;
Huang, JK ;
Stevens, ED ;
Nolan, SP .
ORGANOMETALLICS, 1999, 18 (18) :3760-3763
[18]  
Laubender M, 1999, CHEM-EUR J, V5, P2937, DOI 10.1002/(SICI)1521-3765(19991001)5:10<2937::AID-CHEM2937>3.0.CO
[19]  
2-0
[20]  
Maddock SM, 2001, ANGEW CHEM INT EDIT, V40, P2138, DOI 10.1002/1521-3773(20010601)40:11<2138::AID-ANIE2138>3.0.CO