CHIRAL SULFUR-COMPOUNDS .21. SYNTHESIS AND CONJUGATE AND 1,2 ADDITION-REACTIONS OF A STERICALLY HINDERED ALLYLIC SULFOXIMINE

被引：19

作者：

PYNE, SG ^{[1
]}

BOCHE, G ^{[1
]}

机构：

[1] UNIV MARBURG,FACHBEREICH CHEM,W-3550 MARBURG,GERMANY

来源：

TETRAHEDRON | 1993年 / 49卷 / 37期

关键词：

D O I：

10.1016/S0040-4020(01)81928-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of allylic sulfoximines 3. and 4 is described. The conjugate addition reactions of lithiated 4 with cyclic and acyclic Michael acceptors gives mainly 1,4-gamma and 1,4-alpha adducts respectively in THF and 1,4-alpha and 1,4-gamma adducts respectively in HMPA/THF. The reaction of lithiated 4 and benzaldehyde gives only 1,2-alpha adducts in THF, however 1,2-alpha and 1,2-gamma adducts were isolated when HMPA/THF was employed as solvent. Benzophenone gave only the 1,2-gamma adduct.

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页码：8449 / 8464

页数：16

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[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] CONJUGATE ADDITION OF THE ANION DERIVED FROM 3-(PHENYLSULFINYL)PROP-1-ENE TO CYCLOPENT-2-EN-1-ONE [J].

BINNS, MR ;

HAYNES, RK ;

HOUSTON, TL ;

JACKSON, WR .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1981, 34 (11) :2465-2467

[3] 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

[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] SYNTHESIS OF OPTICALLY-ACTIVE SULFOXIMINES FROM OPTICALLY-ACTIVE SULFOXIDES [J].

JOHNSON, CR ;

KIRCHHOF.RA ;

CORKINS, HG .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (16) :2458-2459

[10] 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