Regioselectivity in a highly efficient, microwave-assisted epoxide aminolysis

被引:45
作者
Desai, Hinal [1 ]
D'Souza, Brendan R. [1 ]
Foether, Devin [1 ]
Johnson, Benjamin F. [1 ]
Lindsay, Harriet A. [1 ]
机构
[1] Eastern Michigan Univ, Dept Chem, Ypsilanti, MI 48197 USA
来源
SYNTHESIS-STUTTGART | 2007年 / 06期
关键词
amino alcohols; amines; epoxides; regioselectivity; solvent effects;
D O I
10.1055/s-2007-965927
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have developed a microwave-assisted aminolysis of epoxides as an efficient method for synthesizing a number of 0-amino alcohols. In most cases, including in reactions of amines with a trisubstituted epoxide, only one equivalent of amine is required to obtain good yields. The reactions are consistently regioselective for amine nucleophiles of varying strengths and for both hindered and unhindered epoxides. In some cases, this regioselectivity could be enhanced by using a polar aprotic or a non-polar solvent.
引用
收藏
页码:902 / 910
页数:9
相关论文
共 83 条
[51]   YTTERBIUM TRIFLATE AND HIGH PRESSURE-MEDIATED RING-OPENING OF EPOXIDES WITH AMINES [J].
MEGURO, M ;
ASAO, N ;
YAMAMOTO, Y .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (18) :2597-2601
[52]   Highly enantioselective synthesis of β-amino alcohols [J].
Metro, Thomas-Xavier ;
Appenzeller, Jerome ;
Pardo, Domingo Gomez ;
Cossy, Janine .
ORGANIC LETTERS, 2006, 8 (16) :3509-3512
[53]   Ammonium decatungstocerate (IV): an efficient catalyst for ring opening of epoxides with aromatic amines [J].
Mirkhani, V ;
Tangestaninejad, S ;
Yadollahi, B ;
Alipanah, L .
CATALYSIS LETTERS, 2005, 101 (1-2) :93-97
[54]   Microwave-assisted aminolysis of epoxides under solvent-free conditions catalyzed by montmorillonite clay [J].
Mojtahedi, MM ;
Saidi, MR ;
Bolourtchian, M .
JOURNAL OF CHEMICAL RESEARCH, 1999, (02) :128-129
[55]   Microwave assisted synthesis -: a critical technology overview [J].
Nüchter, M ;
Ondruschka, B ;
Bonrath, W ;
Gum, A .
GREEN CHEMISTRY, 2004, 6 (03) :128-141
[56]  
O'Brien P, 1999, ANGEW CHEM INT EDIT, V38, P326, DOI 10.1002/(SICI)1521-3773(19990201)38:3<326::AID-ANIE326>3.0.CO
[57]  
2-T
[58]   ZEOLITE-CATALYZED RING-OPENING OF EPOXIDES WITH AMINES [J].
ONAKA, M ;
KAWAI, M ;
IZUMI, Y .
CHEMISTRY LETTERS, 1985, (06) :779-782
[59]   SYNTHESIS APPLICATIONS OF AZA-COPE REARRANGEMENTS .11. CARBON CARBON BOND FORMATION UNDER MILD CONDITIONS VIA TANDEM CATIONIC AZA-COPE REARRANGEMENT MANNICH REACTIONS - A CONVENIENT SYNTHESIS OF POLYSUBSTITUTED PYRROLIDINES [J].
OVERMAN, LE ;
KAKIMOTO, M ;
OKAZAKI, ME ;
MEIER, GP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (22) :6622-6629
[60]   Zinc-catalyzed aminolysis of epoxides [J].
Pachón, LD ;
Gamez, P ;
van Brussel, JJM ;
Reedijk, J .
TETRAHEDRON LETTERS, 2003, 44 (32) :6025-6027