DIASTEREOSELECTIVE CONJUGATE ADDITIONS REACTIONS OF A LITHIATED ALLYLIC SULFOXIMINE TO ACYCLIC ENONES

被引：21

作者：

PYNE, SG ^{[1
]}

DONG, ZM ^{[1
]}

SKELTON, BW ^{[1
]}

WHITE, AH ^{[1
]}

机构：

[1] UNIV WESTERN AUSTRALIA,DEPT CHEM,NEDLANDS,WA 6009,AUSTRALIA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1994年 / 06期

关键词：

D O I：

10.1039/c39940000751

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The conjugate addition reactions of lithiated N-p-tosyl S-phenyl S-prop-2-enyl sulfoximine 4 with cyclic and acyclic enones gives exclusively 1,4-alpha adducts, the reactions with acyclic enones are highly diastereoselective.

引用

页码：751 / 752

页数：2

共 14 条

[1] ASYMMETRIC INDUCTION IN THE ADDITIONS OF ANIONS OF ALLYLIC SULFOXIDES TO BENZALDEHYDE [J].

ANTONJUK, DJ ;

RIDLEY, DD ;

SMAL, MA .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1980, 33 (12) :2635-2651

[2] APROTIC CONJUGATE ADDITION OF ALLYLLITHIUM REAGENTS BEARING POLAR GROUPS TO CYCLIC ENONES .1. 3-ALKYLALLYL SYSTEMS [J].

BINNS, MR ;

HAYNES, RK ;

KATSIFIS, AG ;

SCHOBER, PA ;

VONWILLER, SC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (16) :5411-5423

[3] THE STRUCTURE OF LITHIUM COMPOUNDS OF SULFONES, SULFOXIMIDES, SULFOXIDES, THIOETHERS AND 1,3-DITHIANES, NITRILES, NITRO-COMPOUNDS AND HYDRAZONES [J].

BOCHE, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (03) :277-297

[4] REGIOSELECTIVE AND ENANTIOSELECTIVE SUBSTITUTION OF ALLYLIC SULFOXIMINES WITH ORGANOCOPPER REAGENTS - A VERSATILE APPROACH TO OPTICALLY-ACTIVE ISOCARBACYCLINS [J].

BUND, J ;

GAIS, HJ ;

ERDELMEIER, I .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (04) :1442-1444

[5] ALLYLIC SULFOXIDES - USEFUL INTERMEDIATES IN ORGANIC SYNTHESIS [J].

EVANS, DA ;

ANDREWS, GC .

ACCOUNTS OF CHEMICAL RESEARCH, 1974, 7 (05) :147-155

[6] SYNTHESIS, DEPROTONATION, AND ALKYLATION OF S-ALLYL SULFOXIMINES [J].

HARMATA, M ;

CLAASSEN, RJ .

TETRAHEDRON LETTERS, 1991, 32 (45) :6497-6500

[7] REGIOSELECTIVE CONJUGATE ADDITION OF SULFONYLALLYL CARBANIONS TO ALPHA,BETA-UNSATURATED KETONES [J].

HIRAMA, M .

TETRAHEDRON LETTERS, 1981, 22 (20) :1905-1908

[8] ASYMMETRIC INDUCTION IN THE ADDITION-REACTIONS OF CHIRAL SULFINYLALLYL ANIONS (AMBIDENT NUCLEOPHILES) WITH ENONES (AMBIDENT ELECTROPHILES) - RING-CLOSURE OF ENOL THIOETHER KETONES [J].

HUA, DH ;

VENKATARAMAN, S ;

COULTER, MJ ;

SINAIZINGDE, G .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (05) :719-728

[9] NUCLEOPHILIC-SUBSTITUTION AT SULFUR IN SULFONIMIDOYL COMPOUNDS - SYNTHESIS OF SULFOXIMINES [J].

JOHNSON, CR ;

JONSSON, EU ;

WAMBSGANS, A .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (13) :2061-2065

[10]

KAUS GA, 1978, SYN COMMUN, V8, P483

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