X=Y-ZH systems as potential 1,3-dipoles .48. Enantiopure cycloadducts from oxime-nitrone-isoxazolidine cascades

被引：32

作者：

Dondas, HA ^{[1
]}

Frederickson, M ^{[1
]}

Grigg, R ^{[1
]}

Markandu, J ^{[1
]}

ThorntonPett, M ^{[1
]}

机构：

[1] UNIV LEEDS,SCH CHEM,LEEDS LS2 9JT,W YORKSHIRE,ENGLAND

来源：

TETRAHEDRON | 1997年 / 53卷 / 42期

关键词：

D O I：

10.1016/S0040-4020(97)00919-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiopure cycloadducts have been prepared in good yield via oxime-nitrone-isoxazolidine cascade reactions involving the nucleophilic opening of enantiopure epoxides with oximes followed by 1,3-dipolar cycloaddition reactions with suitable dipolarophiles. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：14339 / 14354

页数：16

相关论文

共 9 条

[1] PREPARATION OF CAMPHOLENAL ANALOGS - CHIRONS FOR THE LIPOPHILIC MOIETY OF SANDALWOOD-LIKE ODORANT ALCOHOLS [J].

CHAPUIS, C ;

BRAUCHLI, R .

HELVETICA CHIMICA ACTA, 1992, 75 (05) :1527-1546

[2]

COLONGE J, 1955, B SOC CHIM FR, P953

[3] Optically active isoxazolidines via asymmetric cycloaddition reactions of nitrones with alkenes: Applications in organic synthesis [J].

Frederickson, M .

TETRAHEDRON, 1997, 53 (02) :403-425

[4] CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION [J].

GAO, Y ;

HANSON, RM ;

KLUNDER, JM ;

KO, SY ;

MASAMUNE, H ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5765-5780

[5] 1,3-AZAPROTIO CYCLOTRANSFER - NITRONE-FORMING OXIME ALKYNE CYCLIZATIONS [J].

GRIGG, R ;

PERRIOR, TR ;

SEXTON, GJ ;

SURENDRAKUMAR, S ;

SUZUKI, T .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (04) :372-374

[6] PREPARATION OF (2R,3S)-1,2-EPOXYPENT-4-EN-3-OL, A NEW CHIRAL BUILDING BLOCK FOR THE SYNTHESIS OF (+)-ENDO-BREVICOMIN AND (-)-EXO-BREVICOMIN [J].

HATAKEYAMA, S ;

SAKURAI, K ;

TAKANO, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (24) :1759-1761

[7]

MARKANDU J, 1997, IN PRESS TETRAHEDRON, P53

[8] PHASE ANNEALING IN SHELX-90 - DIRECT METHODS FOR LARGER STRUCTURES [J].

SHELDRICK, GM .

ACTA CRYSTALLOGRAPHICA SECTION A, 1990, 46 :467-473

[9] LEWIS ACID CATALYSIS OF ENE REACTIONS [J].

SNIDER, BB .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (02) :255-256