A simple, effective and highly selective cleavage of 3-methylbut-2-enyl (prenyl) ethers using p-toluenesulfonic acid

被引:17
作者
Babu, KS [1 ]
Raju, BC [1 ]
Srinivas, PV [1 ]
Sridhar, A [1 ]
Kumar, SP [1 ]
Madhusudana, J [1 ]
机构
[1] Indian Inst Chem Technol, Div Organ Chem 1, Nat Prod Lab, Hyderabad 500007, Andhra Pradesh, India
关键词
D O I
10.1246/cl.2003.704
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A highly selective cleavage of prenyl ethers has been achieved in high yields using p-toluenesulfonic acid under extremely mild conditions. This method is compatible with a wide variety of functional groups such as methyl, benzyl, allyl ethers and benzyl, methyl, prenyl esters present in the molecules.
引用
收藏
页码:704 / 705
页数:2
相关论文
共 9 条
[1]   Highly efficient and chemoselective cleavage of prenyl ethers using ZrCl4/NaBH4 [J].
Babu, KS ;
Raju, BC ;
Srinivas, PV ;
Rao, JM .
TETRAHEDRON LETTERS, 2003, 44 (12) :2525-2528
[2]  
Greene T. W., 1999, PROTECTING GROUPS OR
[3]   p-toluenesulfonic acid-catalyzed efficient synthesis of dihydropyrimidines:: Improved high yielding protocol for the Biginelli reaction [J].
Jin, TS ;
Zhang, SL ;
Li, TS .
SYNTHETIC COMMUNICATIONS, 2002, 32 (12) :1847-1851
[4]  
Kocienski P.J., 1994, PROTECTING GROUPS
[5]   Microwave assisted solvent-free synthesis of pyrazolo[3,4-b]quinolines and pyrazolo[3,4-c]pyrazoles using p-TsOH [J].
Paul, S ;
Gupta, M ;
Gupta, R ;
Loupy, A .
TETRAHEDRON LETTERS, 2001, 42 (23) :3827-3829
[6]   A mild and highly selective deprotective method of prenyl ethers using ytterbium triflate [J].
Sharma, GVM ;
Ilangovan, A ;
Mahalingam, AK .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (24) :9103-9104
[7]   Highly selective cleavage of prenyl ethers by means of a TiCl4- n-Bu4NI mixed reagent [J].
Tsuritani, T ;
Shinokubo, H ;
Oshima, K .
TETRAHEDRON LETTERS, 1999, 40 (46) :8121-8124
[8]  
Vatèle JM, 2002, SYNLETT, P507
[9]  
Vatèle JM, 2001, SYNLETT, P1989