Preparation and synthetic applications of enantiopure (2S,3S)- or (2R,3S)-2-halomethyl-1,2-epoxyalkan-3-amines

被引：22

作者：

Barluenga, J ^{[1
]}

Baragaña, B ^{[1
]}

Concellón, JM ^{[1
]}

机构：

[1] Univ Oviedo, Inst Univ Quim Organomet Enrique Molesd, Oviedo 33071, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 08期

关键词：

D O I：

10.1021/jo9823590

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiomerically pure (2S,3S)-3 and its diastereoisomer (2R,3S)-2-halomethyl-1,2-epoxyalkan-3-amine 4 have been obtained from 1-aminoalkyl halomethyl ketones 1 and (iodomethyl)lithium or (chloromethyl)lithium, respectively. Some synthetic applications of compounds 3 are described: chiral unsaturated 1,3-aminoalcohols 8 or 2-(halomethylidene)-3-(dibenzylamino)-alkan-1-ol 11 is obtained from 3 by halogeno-lithium or by hydrogen-lithium exchange, respectively. Transformation of 8c into its methyl ester derivative 9c is also reported.

引用

页码：2843 / 2846

页数：4

共 32 条

[1] Synthesis and reactions of enantiomerically pure chloromethyl oxiranes [J].

Abrate, F ;

Bravo, P ;

Frigerio, M ;

Viani, F ;

Zanda, M .

TETRAHEDRON-ASYMMETRY, 1996, 7 (02) :581-594

[2] STEREOCONTROLLED SYNTHESIS OF ERYTHRO N-PROTECTED ALPHA-AMINO EPOXIDES AND PEPTIDYL EPOXIDES [J].

ALBECK, A ;

PERSKY, R .

TETRAHEDRON, 1994, 50 (21) :6333-6346

[3] Lithium trifluoromethanesulfonate-catalysed aminolysis of oxiranes [J].

Auge, J ;

Leroy, F .

TETRAHEDRON LETTERS, 1996, 37 (43) :7715-7716

[4] THE FIRST DIRECT PREPARATION OF CHIRAL FUNCTIONALIZED KETONES AND THEIR SYNTHETIC USES [J].

BARLUENGA, J ;

BARAGANA, B ;

ALONSO, A ;

CONCELLON, JM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (08) :969-970

[5] Synthetic applications of 1-aminoalkyl chloromethyl ketones. Synthesis of enantiopure 3-azetidinols and aminoalkyl epoxides [J].

Barluenga, J ;

Baragana, B ;

Concellon, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :5974-5977

[6] HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF THREO OR ERYTHRO AMINOALKYL EPOXIDES FROM ALPHA-AMINO-ACIDS [J].

BARLUENGA, J ;

BARAGANA, B ;

CONCELLON, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :6696-6699

[7]

BARLUENGA J, 1995, TETRAHEDRON, V51, P5573

[8]

BARLUENGA J, UNPUB

[9]

Behrens C. H., 1983, ALDRICHIM ACTA, V16, P67

[10] C-1 REACTIVITY OF 2,3-EPOXY ALCOHOLS VIA OXIRANE OPENING WITH METAL-HALIDES - APPLICATIONS AND SYNTHESIS OF NATURALLY-OCCURRING 2,3-OCTANEDIOL, MURICATACIN, 3-OCTANOL, AND 4-DODECANOLIDE [J].

BONINI, C ;

FEDERICI, C ;

ROSSI, L ;

RIGHI, G .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (15) :4803-4812

← 1 2 3 4 →