Solid lithium perchlorate as a powerful catalyst for the synthesis of β-aminoalcohols under solvent-free conditions

被引:18
作者
Azizi, N [1 ]
Saidi, MR [1 ]
机构
[1] Sharif Univ Technol, Dept Chem, Tehran, Iran
关键词
epoxide; lithium perchlorate; beta-aminoalcohols; solvent-free;
D O I
10.1139/V05-062
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Lithium perchlorate catalyzed the ring opening of epoxides with amines to provide the corresponding beta-aminoalcohols in excellent yields with high regioselectivity. The reaction proceeds rapidly under mild and neutral conditions and worked well with primary, secondary, aliphatic, aromatic, and hindered amines in short times at room temperature, in the absence of solvent.
引用
收藏
页码:505 / 507
页数:3
相关论文
共 30 条
[1]   1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].
Ager, DJ ;
Prakash, I ;
Schaad, DR .
CHEMICAL REVIEWS, 1996, 96 (02) :835-875
[2]   Unraveling the mechanism of epoxide formation from sulfur ylides and aldehydes [J].
Aggarwal, VK ;
Harvey, JN ;
Richardson, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (20) :5747-5756
[3]   LiClO4 accelerated Michael addition of amines to α,β-unsaturated olefins under solvent-free conditions [J].
Azizi, N ;
Saidi, MR .
TETRAHEDRON, 2004, 60 (02) :383-387
[4]   Lithium perchlorate-catalyzed three-component coupling:: A facile and general method for the synthesis of α-aminophosphonates under solvent-free conditions [J].
Azizi, N ;
Saidi, MR .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (23) :4630-4633
[5]   REGIOSELECTIVE AND CHEMOSELECTIVE SYNTHESIS OF HALOHYDRINS BY CLEAVAGE OF OXIRANES WITH METAL-HALIDES [J].
BONINI, C ;
RIGHI, G .
SYNTHESIS-STUTTGART, 1994, (03) :225-238
[6]   An efficient synthesis of 2-amino alcohols by silica gel catalysed opening of epoxide rings by amines [J].
Chakraborti, AK ;
Rudrawar, S ;
Kondaskar, A .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (09) :1277-1280
[7]   ZrCl4 as a new and efficient catalyst for the opening of epoxide rings by amines [J].
Chakraborti, AK ;
Kondaskar, A .
TETRAHEDRON LETTERS, 2003, 44 (45) :8315-8319
[8]  
Chandrasekhar S, 2000, SYNTHESIS-STUTTGART, P1817
[9]   REGIOALTERNATING SELECTIVITY IN THE METAL SALT CATALYZED AMINOLYSIS OF STYRENE OXIDE [J].
CHINI, M ;
CROTTI, P ;
MACCHIA, F .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5939-5942
[10]   METAL-SALTS AS NEW CATALYSTS FOR MILD AND EFFICIENT AMINOLYSIS OF OXIRANES [J].
CHINI, M ;
CROTTI, P ;
MACCHIA, F .
TETRAHEDRON LETTERS, 1990, 31 (32) :4661-4664