Synthesis of chiral amino epoxyaziridines:: Useful intermediates for the preparation of chiral trisubstituted piperidines

被引：25

作者：

Concellón, JM

Riego, E

Rivero, IA

Ochoa, A

机构：

[1] Univ Oviedo, Fac Quim, Dept Quim Organ & Inorgan, Oviedo 33071, Spain

[2] Ctr Grad & Invest, Inst Tecnol Tijuana, Tijuana 22000, BC, Mexico

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 19期

关键词：

D O I：

10.1021/jo0490806

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral aminoalkyl epoxyaziridine 1 is synthesized in high yield and diastereoselectivity from L-serine. Ring opening of epoxyaziridine 1 with primary amines is carried out with total chemo- and regioselectivity, affording chiral polyfunctionalized piperidines 8. The structure of these trisubstituted piperidines is established by NMR studies.

引用

收藏

页码：6244 / 6248

页数：5

相关论文

共 29 条

[1]

Angle S. R., 1995, STUD NAT PROD CHEM, V16, P453

[2]

[Anonymous], 1985, ALKALOIDS CHEM BIOL

[3] Asymmetric routes to substituted piperidines [J].

Bailey, PD ;

Millwood, PA ;

Smith, PD .

CHEMICAL COMMUNICATIONS, 1998, (06) :633-640

[4]

BANFI L, 1993, SYNTHESIS-STUTTGART, P1029

[5] 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

[6] trans-6-aminocyclohept-3-enols, a new designed polyfunctionalized chiral building block for the asymmetric synthesis of 2-substituted-4-hydroxypiperidines [J].

Celestini, P ;

Danieli, B ;

Lesma, G ;

Sacchetti, A ;

Silvani, A ;

Passarella, D ;

Virdis, A .

ORGANIC LETTERS, 2002, 4 (08) :1367-1370

[7] Ring opening of nonactivated 2-(1-aminoalkyl) aziridines:: Unusual regio- and stereoselective C-2 and C-3 cleavage [J].

Concellón, JM ;

Riego, E .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16) :6407-6410

[8] Regio- and stereoselective C-2 and C-3 cleavage of 2-(1-aminoalkyl)aziridines with alcohols, carboxylic acids, and sodium iodide [J].

Concellón, JM ;

Riego, E ;

Suárez, JR .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) :9242-9246

[9] An improved preparation of epoxides from carbonyl compounds by using diiodomethane/methyllithium:: synthetic applications [J].

Concellón, JM ;

Cuervo, H ;

Fernández-Fano, R .

TETRAHEDRON, 2001, 57 (43) :8983-8987

[10] Enantiopure preparation of the two enantiomers of the pseudo-C2-symmetric N,N-dibenzyl-1,2:4,5-diepoxypentan-3-amine [J].

Concellón, JM ;

Riego, E ;

Rodríguez-Solla, H ;

Plutin, AM .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (25) :8661-8665