HIGHLY STEREOSELECTIVE PREPARATION OF TRI-SUBSTITUTED AND TETRA-SUBSTITUTED OLEFINS VIA BETA-TRIBUTYLSTANNYL-ALPHA,BETA-UNSATURATED KETONES

被引：26

作者：

TAKEDA, T

KABASAWA, Y

FUJIWARA, T

机构：

[1] Department of Applied Chemistry, Tokyo University of Agriculture and Technology, Koganei, Tokyo

来源：

TETRAHEDRON | 1995年 / 51卷 / 09期

关键词：

D O I：

10.1016/0040-4020(95)00016-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium(0)-catalyzed reactions of beta-tributylstannyl-alpha,beta-unsaturated ketones 3 with benzyl or aryl halides in the presence of copper(I) iodide gave the tri- and tetra-substituted olefins 4 or 5 with high stereoselectivity, respectively. It was found that the yields of 5 were remarkably improved by the use of triethylamine as an additive. The starting materials 3 were easily prepared by the tin(IV) chloride-promoted coupling reaction of alpha-tributylstannylthioacetals with enol silyl ethers followed by the treatment with potassium hydride or DBU in good yields.

引用

页码：2515 / 2524

页数：10

共 55 条

[41] STEREOSELECTIVE CONJUGATE ADDITION OF LITHIUM (PHENYLTHIO)(TRIMETHYLSTANNYL) CUPRATE TO ALPHA,BETA-ACETYLENIC ESTERS - PREPARATION OF (E)-4-LITHIO-1,3-PENTADIENES AND (Z)-4-LITHIO-1,3-PENTADIENES AND THEIR REACTION WITH ELECTROPHILES
PIERS, E
MORTON, HE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (21) : 4263 - 4264
[42] REUCROFT J, 1971, QUART REV LONDON, V25, P135
[43] ALKYLATION OF BETA-SUBSTITUTED STYRENES BY A FREE-RADICAL ADDITION ELIMINATION SEQUENCE
RUSSELL, GA
TASHTOUSH, H
NGOVIWATCHAI, P
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (16) : 4622 - 4623
[44] PALLADIUM-CATALYZED CROSS-COUPLING SYNTHESIS OF HINDERED BIARYLS AND TERPHENYLS - COCATALYSIS BY COPPER(I) SALTS
SAA, JM
MARTORELL, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (07) : 1963 - 1966
[45] SAIHI ML, 1977, B SOC CHIM FR II-CH, P1251
[46] NOVEL CONVERSION OF E-STEREOSELECTIVITY TO Z-STEREOSELECTIVITY IN TRIFLUOROMETHYLATED ALPHA,BETA-UNSATURATED ESTERS AND NITRILES BY WAY OF O-METHYLATION OF AN YLIDE ANION
SHEN, YC
GAO, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (11): : 1473 - 1475
[47] Sonogashira K., 1991, COMPREHENSIVE ORGANI, V3, P521, DOI DOI 10.1016/B978-0-08-052349-1.00071-8
[48] PALLADIUM CATALYZED COUPLING OF ORGANOTIN REAGENTS WITH ORGANIC ELECTROPHILES
STILLE, JK
[J]. PURE AND APPLIED CHEMISTRY, 1985, 57 (12) : 1771 - 1780
[49] HIGHLY STEREOSELECTIVE SYNTHESIS OF EXOCYCLIC TETRASUBSTITUTED ENOL ETHERS AND OLEFINS - A SYNTHESIS OF NILEPROST
TAKAHASHI, A
KIRIO, Y
SODEOKA, M
SASAI, H
SHIBASAKI, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (02) : 643 - 647
[50] Z-SELECTIVE FORMATION OF TRISUBSTITUTED ALPHA,BETA-UNSATURATED NITRILE BY THE HORNER-EMMONS REACTION
TAKAYANAGI, H
[J]. TETRAHEDRON LETTERS, 1994, 35 (10) : 1581 - 1584

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