Gold-catalyzed intramolecular hydroalkoxylation/cyclization of conjugated dienyl alcohols

被引：6

作者：

Chandrasekhar, B.

Ryu, Jae-Sang ^{[1
]}

机构：

[1] Ewha Womans Univ, Coll Pharm, Ctr Cell Signaling & Drug Discovery Res, Seoul 120750, South Korea

来源：

TETRAHEDRON | 2012年 / 68卷 / 24期

关键词：

Hydroalkoxylation; Conjugated diene; Alcohol; Gold; Cyclization; SATURATED OXYGEN HETEROCYCLES; TRIFLATE IONIC LIQUIDS; REACTION-MECHANISM; CARBOXYLIC-ACIDS; ALKYNYL ALCOHOLS; NATURAL-PRODUCTS; CYCLIC ETHERS; HYDROAMINATION; DERIVATIVES; ALLENES;

D O I：

10.1016/j.tet.2012.03.120

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic intramolecular additions of hydroxyl groups to tethered conjugated dienes are described. The reactions proceed smoothly at 60 degrees C in the presence of 5 mol % of (PPh3)AuCl/AgOTf as a catalyst. A broad range of structurally diverse conjugated dienes produce substituted tetrahydrofurans and tetrahydropyrans in good yields. This reaction represents an atom-economic route to construct five- and six-membered cyclic ethers. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：4805 / 4812

页数：8

共 48 条

[21] Palladium/benzoic acid-catalyzed hydroalkoxylation of alkynes
Kadota, I
Lutete, LM
Shibuya, A
Yamamoto, Y
[J]. TETRAHEDRON LETTERS, 2001, 42 (35) : 6207 - 6210
[22] Copper-Catalyzed Intramolecular Hydroalkoxylation of α-(1-Hydroxy-1-alkyl- and -aryl)methylallenoates by a 5-Endo Mode for Preparation of 2-Alkyl- and 2-Aryl-2,5-dihydrofurans
Kim, Sanghyuck
Lee, Phil Ho
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (01) : 215 - 220
[23] Cyclization of allenyne-1,6-diols catalyzed by gold and silver salts: An efficient selective synthesis of dihydrofuran and furan derivatives
Kim, Sundae
Lee, Phil Ho
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (04) : 547 - 551
[24] Gold-catalyzed cyclization of enyne-1,6-diols to substituted furans
Kim, Sundae
Kang, Dongjin
Shin, Seunghoon
Lee, Phil Ho
[J]. TETRAHEDRON LETTERS, 2010, 51 (14) : 1899 - 1901
[25] KOTSUKI H, 1992, SYNLETT, P97
[26] The reaction mechanism of the hydroamination of alkenes catalyzed by gold(I)-phosphine:: The role of the counterion and the N-nucleophile substituents in the proton-transfer step
Kovacs, Gabor
Ujaque, Gregori
Lledos, Agusti
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (03) : 853 - 864
[27] Phosphine gold(I)-catalyzed hydroamination of alkenes under thermal and microwave-assisted conditions
Liu, Xin-Yuan
Li, Cheng-Hui
Che, Chi-Ming
[J]. ORGANIC LETTERS, 2006, 8 (13) : 2707 - 2710
[28] Atom-Efficient Carbon-Oxygen Bond Formation Processes. DFT Analysis of the Intramolecular Hydroalkoxylation/Cyclization of Alkynyl Alcohols Mediated by Lanthanide Catalysts
Motta, Alessandro
Fragala, Ignazio L.
Marks, Tobin J.
[J]. ORGANOMETALLICS, 2010, 29 (09) : 2004 - 2012
[29] Highly efficient gold-catalyzed atom-economical annulation of phenols with dienes
Nguyen, Rene-Viet
Yao, Xiaoquan
Li, Chao-Jun
[J]. ORGANIC LETTERS, 2006, 8 (11) : 2397 - 2399
[30] Palladium-catalyzed intramolecular asymmetric hydroamination, hydroalkoxylation, and hydrocarbonation of alkynes
Patil, Nitin T.
Lutete, Leopold Mpaka
Wu, Huanyou
Pahadi, Nirmal K.
Gridnev, Ilya D.
Yamamoto, Yoshinori
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (11) : 4270 - 4279

← 1 2 3 4 5 →