Regioselective Synthesis of tert-Allylic Ethers via Gold(I)-Catalyzed Intermolecular Hydroalkoxylation of Allenes

被引:61
作者
Hadfield, Maximillian S. [1 ]
Lee, Ai-Lan [1 ]
机构
[1] Heriot Watt Univ, Sch Engn & Phys Sci, Edinburgh EH14 4AS, Midlothian, Scotland
基金
英国工程与自然科学研究理事会;
关键词
GOLD-CATALYZED CYCLOISOMERIZATION; DERIVATIVES; CYCLIZATION; EFFICIENT; ALCOHOL; HYDROXYALLENES; OPPORTUNITIES; HETEROCYCLES; CARBOCYCLES; REDUCTION;
D O I
10.1021/ol902675k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly regloselective method towards tertiary allylic ethers via gold(I)-catalyzed intermolecular hydroalkoxylation of allenes is disclosed. Preventing subsequent Isomerization of the tertiary allylic ether products to primary allylic ethers appears to be the key to achieving high regioselectivities.
引用
收藏
页码:484 / 487
页数:4
相关论文
共 46 条
[1]   Metal-catalyzed regiodivergent cyclization of γ-allenols:: Tetrahydrofurans versus oxepanes [J].
Alcaide, Benito ;
Almendros, Pedro ;
del Campo, Teresa Martinez .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (35) :6684-6687
[2]   Kinetics of liquid phase synthesis of ethyl tert-butyl ether from tert-butyl alcohol and ethanol catalyzed by β-zeolite supported on monolith [J].
Assabumrungrat, S ;
Kiatkittipong, W ;
Sevitoon, N ;
Praserthdam, P ;
Goto, S .
INTERNATIONAL JOURNAL OF CHEMICAL KINETICS, 2002, 34 (05) :292-299
[3]   Gold catalysed reactions with cyclopropenes [J].
Bauer, Juergen T. ;
Hadfield, Maximillian S. ;
Lee, Ai-Lan .
CHEMICAL COMMUNICATIONS, 2008, (47) :6405-6407
[4]   NATURALLY-OCCURRING TERPENE DERIVATIVES .379. FURTHER INEUPATOROLIDE-LIKE GERMACRANOLIDES FROM INULA-CUSPIDATA [J].
BOHLMANN, F ;
SINGH, P ;
JAKUPOVIC, J .
PHYTOCHEMISTRY, 1982, 21 (01) :157-160
[5]   Gold(I)-catalyzed formation of 4-alkylidene-1,3-dioxolan-2-ones from propargylic tert-butyl carbonates [J].
Buzas, A ;
Gagosz, F .
ORGANIC LETTERS, 2006, 8 (03) :515-518
[6]   Gold(I)-catalyzed formation of 5-methylene-1,3-oxazolidin-2-ones [J].
Buzas, Andrea ;
Gagosz, Fabien .
SYNLETT, 2006, (17) :2727-2730
[7]   A general method for the preparation of ethers using water-resistant solid Lewis acids [J].
Corma, Avelino ;
Renz, Michael .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (1-2) :298-300
[8]   Regio- and Stereoselective Au(I)-Catalyzed Intermolecular Hydroalkoxylation of Aryl Allenes [J].
Cui, Dong-Mei ;
Yu, Ke-Rui ;
Zhang, Chen .
SYNLETT, 2009, (07) :1103-1106
[9]   Gold-Catalyzed Hydroalkoxylation of Alkoxyallenes [J].
Cui, Dong-Mei ;
Zheng, Zhi-Ling ;
Zhang, Chen .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (03) :1426-1427
[10]   Golden opportunities in stereoselective catalysis:: Optimization of chirality transfer and catalyst efficiency in the gold-catalyzed cycloisomerization of α-hydroxyallenes to 2,5-dihydrofurans [J].
Deutsch, Carl ;
Gockel, Birgit ;
Hoffmann-Roeder, Anja ;
Krause, Norbert .
SYNLETT, 2007, (11) :1790-1794