HIGHLY STEREOSELECTIVE PREPARATION OF BETA-(ORGANOTELLURO)ACROLEINS AND FACILE STEREOSPECIFIC SYNTHESIS OF CONJUGATED DIENOLS

被引：53

作者：

MO, XS ^{[1
]}

HUANG, YZ ^{[1
]}

机构：

[1] CHINESE ACAD SCI,SHANGHAI INST ORGAN CHEM,ORGANOMET CHEM LAB,SHANGHAI 200032,PEOPLES R CHINA

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 20期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1016/0040-4039(95)00580-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diorganoditellurides 1 (1a R = n-Bu;1b R = Ph), by treated with sodium borohydride, reacted with propargylaldehyde to give corresponding beta-(organotelluro)acroleins 2 with high (Z)-stereoselectivity in good yields (2a: Z : E = 89 : 11; 2b: pure Z-isomer); Tellurides 3, on treatment with n-BuLi, reacted with carbonyl compounds to afford conjugated dienols with retention of olefin geometry in high yields.

引用

页码：3539 / 3542

页数：4

共 22 条

[1] A SYNTHETIC EQUIVALENT FOR THE BUTADIENYL CARBONIUM-ION - USE OF 4-(TRIMETHYLSILYL)BUT-2-YNAL FOR PREPARATION OF 1,3-DIENES AND MACROEXPANSION OF CYCLIC-KETONES [J].

ANGOH, AG ;

CLIVE, DLJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (08) :534-536

[2]

Back T. G., 1987, CHEM ORGANIC SELENIU, V2, P91

[3] VINYLLITHIUMS FROM BUTYL-VINYL TELLURIDES AND BIS-VINYL TELLURIDES [J].

BARROS, SM ;

COMASSETO, JV ;

BERRIEL, J .

TETRAHEDRON LETTERS, 1989, 30 (52) :7353-7356

[4]

BLOCH R, 1983, TETRAHEDRON LETT, V24, P124

[5] ALPHA-HALOALKANESULFONYL BROMIDES IN ORGANIC-SYNTHESIS .1. FORMATION AND BASE-INDUCED REACTIONS OF ALPHA,BETA-UNSATURATED HALOMETHYL SULFONES [J].

BLOCK, E ;

ASLAM, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (19) :6164-6165

[6] TRANSMETALATION BETWEEN VINYLIC TELLURIDES AND HIGHER-ORDER CYANOCUPRATES - INSITU FORMATION OF VINYL CUPRATES [J].

COMASSETO, JV ;

BERRIEL, JN .

SYNTHETIC COMMUNICATIONS, 1990, 20 (11) :1681-1685

[7] CYCLIZATION OF 3-(ARYLCHALCOGENO)PROPENOYL CHLORIDES .1. 1,2-OXATELLUROL-1-IUM HALIDES VIA IPSO ACYLATION [J].

DETTY, MR ;

MURRAY, BJ ;

SMITH, DL ;

ZUMBULYADIS, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (04) :875-882

[8] 12-TE-5 PERTELLURANES FROM 1,2-OXATELLUROLYL-1-IUM HALIDES - SYNTHESIS, STRUCTURE, AND REACTIVITY - THE QUEST FOR DELOCALIZATION IN 10-TE-3 TELLURANES AND 12-TE-5 PERTELLURANES OF THIATHIOPHTHENE STRUCTURE [J].

DETTY, MR ;

LUSS, HR ;

MCKELVEY, JM ;

GEER, SM .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (10) :1692-1700

[9] SYNTHETIC APPLICATIONS OF ORGANOTELLURIUM CHEMISTRY [J].

ENGMAN, L .

ACCOUNTS OF CHEMICAL RESEARCH, 1985, 18 (09) :274-279

[10]

GOMEZ AM, 1993, SYNLETT, V10, P943

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