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

页码：902 / 910

页数：9

共 83 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] Long-chain formoterol analogues:: an investigation into the effect of increasing amino-substituent chain length on the β2-adrenoceptor activity [J].

Alikhani, V ;

Beer, D ;

Bentley, D ;

Bruce, I ;

Cuenoud, BM ;

Fairhurst, RA ;

Gedeck, P ;

Haberthuer, S ;

Hayden, C ;

Janus, D ;

Jordan, L ;

Lewis, C ;

Smithies, K ;

Wissler, E .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (18) :4705-4710

[3] The preparation of β-substituted amines from mixtures of epoxide opening products via a common aziridinium ion intermediate [J].

Anderson, SR ;

Ayers, JT ;

DeVries, KM ;

Ito, F ;

Mendenhall, D ;

Vanderplas, BC .

TETRAHEDRON-ASYMMETRY, 1999, 10 (14) :2655-2663

[4] Highly chemoselective addition of amines to epoxides in water [J].

Azizi, N ;

Saidi, MR .

ORGANIC LETTERS, 2005, 7 (17) :3649-3651

[5] Solid lithium perchlorate as a powerful catalyst for the synthesis of β-aminoalcohols under solvent-free conditions [J].

Azizi, N ;

Saidi, MR .

CANADIAN JOURNAL OF CHEMISTRY, 2005, 83 (05) :505-507

[6] Epoxide opening with amino acids: improved synthesis of hydroxyethylamine dipeptide isosteres [J].

Babic, A ;

Sova, M ;

Gobec, S ;

Pecar, S .

TETRAHEDRON LETTERS, 2006, 47 (11) :1733-1735

[7] Asymmetric aminolysis of aromatic epoxides:: A facile catalytic enantioselective synthesis of anti-β-amino alcohols [J].

Bartoli, G ;

Bosco, M ;

Carlone, A ;

Locatelli, M ;

Massaccesi, M ;

Melchiorre, P ;

Sambri, L .

ORGANIC LETTERS, 2004, 6 (13) :2173-2176

[8] The synthesis of vicinal amino alcohols [J].

Bergmeier, SC .

TETRAHEDRON, 2000, 56 (17) :2561-2576

[9] A green route to β-amino alcohols via the uncatalyzed aminolysis of 1,2-epoxides by alkyl- and arylamines [J].

Bonollo, Simona ;

Fringuelli, Francesco ;

Pizzo, Ferdinando ;

Vaccaro, Luigi .

GREEN CHEMISTRY, 2006, 8 (11) :960-964

[10] Polystyrene-supported (R)-2-piperazino-1,1,2-triphenylethanol:: A readily available supported ligand with unparalleled catalytic activity and enantioselectivity [J].

Castellnou, D ;

Solà, L ;

Jimeno, C ;

Fraile, JM ;

Mayoral, JA ;

Riera, A ;

Pericàs, MA .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (02) :433-438

← 1 2 3 4 5 6 7 8 9 →