STEREOSPECIFIC DECONJUGATION OF ALKYL (E) AND (Z)-3-TRIMETHYLSTANNYL-2-ALKENOATES

被引：31

作者：

PIERS, E

GAVAI, AV

机构：

[1] Department of Chemistry, University of British Columbia, Vancouver

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 08期

关键词：

D O I：

10.1021/jo00295a027

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of the alkyl (E)-3-trimethylstannyl-2-alkenoates 16a-e with lithium diisopropylamide in tetrahydrofuran, followed by protonation of the resultant enolate anions, affords exclusively the alkyl (Z)-3-trimethylstannyl-3-alkenoates 13a-e, respectively. In similar fashion, the (Z)-2-alkenoates 17a-e are transformed, completely stereoselectively, into the corresponding (E)-3-alkenoates 14a-e. © 1990, American Chemical Society. All rights reserved.

引用

页码：2374 / 2379

页数：6

共 38 条

[1] ON THE CONJUGATIVE ISOMERIZATIONS OF BETA-UNSATURATED, GAMMA-UNSATURATED ESTERS - STEREOCHEMICAL GENERALIZATIONS AND PREDICTIONS FOR 1,3-PROTOTROPIC SHIFTS UNDER BASIC CONDITIONS
ALCOCK, SG
BALDWIN, JE
BOHLMANN, R
HARWOOD, LM
SEEMAN, JI
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (19) : 3526 - 3535
[2] AN UNDERSTANDING OF STEREOSELECTIVITY OF BASE-CATALYZED OLEFIN ISOMERIZATION BASED ON A THERMODYNAMICALLY MORE STABLE CIS-ALLYLIC ANION
BANK, S
SCHRIESH.A
ROWE, CA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (14) : 3244 - &
[3] CROTYLLITHIUM BY DIRECT METALATION - RELATIVE STABILITIES OF Z-CROTYL AND E-CROTYL ANIONS
BATES, RB
BEAVERS, WA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (15) : 5001 - 5002
[4] BERES JA, 1980, EUR J MED CHEM, V15, P571
[5] ABINITIO SCF TREATMENT OF ALLYL ANION AND DISTORTED PROPENYL ANIONS
BOERTH, DW
STREITWIESER, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (03) : 750 - 754
[6] SYNTHESIS OF SUBSTITUTED 5,6-DIHYDRO-2H-PYRAN-2-ONES - PROPIOLIC ACID DIANION AS A REACTIVE 3-CARBON NUCLEOPHILE
CARLSON, RM
OYLER, AR
PETERSON, JR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (11) : 1610 - 1616
[7] COREY EJ, 1972, TETRAHEDRON LETT, P3769
[8] HERRMANN JL, 1973, TETRAHEDRON LETT, P2433
[9] DEPENDENCE OF CONFORMATIONAL AND ISOMER STABILITY ON NUMBER OF ELECTRONS IN EXTENDED PI SYSTEMS
HOFFMANN, R
OLOFSON, RA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (05) : 943 - &
[10] A PRACTICAL SYNTHESIS OF (Z)-3-ALKENOATES
IKEDA, Y
YAMAMOTO, H
[J]. TETRAHEDRON LETTERS, 1984, 25 (45) : 5181 - 5182

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