Concise synthesis of 2,6-disubstituted morpholines by cyclization of epoxy alcohols

被引：17

作者：

Albanese, Domenico

Salsa, Matteo

Landini, Dario

Lupi, Vittoria

Penso, Michele

机构：

[1] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy

[2] ISt CNR, ISTM, I-20133 Milan, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 2007卷 / 13期

关键词：

phase-transfer catalysis; cyclization; sulfonamides; epoxy alcohols; morpholines;

D O I：

10.1002/ejoc.200700011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel, straightforward and high yielding synthesis of enantiomerically pure 2,6-disubstituted morpholines was developed by acid-catalyzed cyclization of epoxy alcohols. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).

引用

页码：2107 / 2113

页数：7

共 24 条

[1] Novel concise synthesis of 2-substituted 3,4-dihydro-2H-1,4-benzoxazines by ring opening of glycidols under solid-liquid phase transfer catalysis conditions [J].

Albanese, D ;

Landini, D ;

Penso, M .

CHEMICAL COMMUNICATIONS, 1999, (20) :2095-2096

[2] New series of morpholine and 1,4-oxazepane derivatives as dopamine D4 receptor ligands:: Synthesis and 3D-QSAR model [J].

Audouze, K ;

Nielsen, EO ;

Peters, D .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (12) :3089-3104

[3]

BALDOLI C, 1995, J ORGANOMET CHEM, V486, P279, DOI 10.1016/0022-328X(94)05111-N

[4] RULES FOR RING-CLOSURE [J].

BALDWIN, JE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736

[5] Stereoselective synthesis of 2,6-disubstituted morpholines from chiral non-racemic lactams [J].

Bouron, E ;

Goussard, G ;

Marchand, C ;

Bonin, M ;

Pannecoucke, X ;

Quirion, JC ;

Husson, HP .

TETRAHEDRON LETTERS, 1999, 40 (40) :7227-7230

[6] Facile route to 3,5-disubstituted morpholines: Enantioselective synthesis of O-protected trans-3,5-bis(hydroxymethyl)morpholines [J].

Dave, R ;

Sasaki, NA .

ORGANIC LETTERS, 2004, 6 (01) :15-18

[7]

ENDERS D, 1993, SYNTHESIS-STUTTGART, P66

[8] BIS[[4-(2,2-DIMETHYL-1,3-DIOXOLYL)]METHYL]-CARBODIIMIDE (BDDC) AND ITS APPLICATION TO RESIDUE-FREE ESTERIFICATIONS, PEPTIDE COUPLINGS, AND DEHYDRATIONS [J].

GIBSON, FS ;

PARK, MS ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (24) :7503-7507

[9] Palladium-catalyzed asymmetric tandem allylic substitution using chiral 2-(phosphinophenyl)pyridine ligand [J].

Ito, K ;

Imahayashi, Y ;

Kuroda, T ;

Eno, S ;

Saito, B ;

Katsuki, T .

TETRAHEDRON LETTERS, 2004, 45 (39) :7277-7281

[10] Efficient, stereoselective synthesis of trans-2,5-disubstituted morpholines [J].

Lanman, BA ;

Myers, AG .

ORGANIC LETTERS, 2004, 6 (06) :1045-1047

← 1 2 3 →