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

被引：138

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 27期

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

页码：7900 / 7901

页数：2

共 20 条

[1] Ruthenium-catalyzed reductive coupling reaction of propargylic alcohols via hydroboration of allenylidene intermediates
Onodera, G
Nishibayashi, Y
Uemura, S
ORGANOMETALLICS, 2006, 25 (01) : 35 - 37
[2] Ruthenium-catalyzed enantioselective prolpargylation of aromatic compounds with propargylic alcohols via allenylidene intermediates
Matsuzawa, Hiroshi
Miyake, Yoshihiro
Nishibayashi, Yoshiaki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (34) : 6488 - 6491
[3] Ruthenium-catalyzed cycloaddition between propargylic alcohols and cyclic 1,3-dicarbonyl compounds via an allenylidene intermediate
Nishibayashi, Y
Yoshikawa, M
Inada, Y
Hidai, M
Uemura, S
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (10): : 3408 - 3412
[4] Ruthenium-Catalyzed Oxygenative Transformation of Terminal Propargyl Alcohols to Metheyleneketenes via Allenylidene Intermediates: Synthesis of α,β-Unsaturated Carboxylic Acid Derivatives
Wang, Xinyu
Li, Qihuan
Wen, Tingbin
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (01) : 284 - 296
[5] Ruthenium-catalyzed carbon-carbon bond formation between propargylic alcohols and alkenes via the allenylidene-ene reaction
Nishibayashi, Y
Inada, Y
Hidai, M
Uemura, S
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (20) : 6060 - 6061
[6] Ruthenium-catalyzed carbon-carbon bond formation between propargylic alcohols and alkenes via the allenylidene-ene reaction
Hidai, M. (uemura@scl.kyoto-u.ac.jp), 1600, American Chemical Society (125):
[7] Ruthenium-Catalyzed Enantioselective [3+3] Cycloaddition of Propargylic Alcohols with 2-Naphthols
Kanao, Keiichiro
Miyake, Yoshihiro
Nishibayashi, Yoshiaki
ORGANOMETALLICS, 2010, 29 (09) : 2126 - 2131
[8] Ruthenium-catalyzed synthesis of alkylidenecyclobutenes via head-to-head dimerization of propargylic alcohols and cyclobutadiene-ruthenium intermediates
Le Paih, J
Dérien, S
Demerseman, B
Bruneau, C
Dixneuf, PH
Toupet, L
Dazinger, G
Kirchner, K
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (04) : 1312 - 1324
[9] Regio- and stereoselective syntheses of piperidine derivatives via ruthenium-catalyzed coupling of propargylic amides and allylic alcohols
Murugesan, Sathiyamoorthy
Jiang, Fan
Achard, Mathieu
Bruneau, Christian
Derien, Sylvie
CHEMICAL COMMUNICATIONS, 2012, 48 (52) : 6589 - 6591
[10] Ruthenium-catalyzed reactions of 1-cyclopropyl-2-propyn-1-ols with anilines and water via allenylidene intermediates: Selective preparation of tri- and tetrasubstituted conjugated enynes
Yamauchi, Yoshihiro
Onodera, Gen
Sakata, Ken
Yuki, Masahiro
Miyake, Yoshihiro
Uemura, Sakae
Nishibayashi, Yoshiaki
Journal of the American Chemical Society, 2007, 129 (16): : 5175 - 5179

← 1 2 →