SYN-SELECTIVE REFORMATSKY-TYPE REACTION OF ALPHA-SILYL-ALPHA-STANNYLACETIC ESTERS WITH ALDEHYDES - STEREOSELECTIVE SYNTHESIS OF (E)-ALPHA,BETA-UNSATURATED ESTERS AND (Z)-ALPHA,BETA-UNSATURATED ESTERS

被引：0

作者：

AKAI, S ^{[1
]}

TSUZUKI, Y ^{[1
]}

MATSUDA, S ^{[1
]}

KITAGAKI, S ^{[1
]}

KITA, Y ^{[1
]}

机构：

[1] OSAKA UNIV,FAC PHARMACEUT SCI,1-6 YAMADA OKA,SUITA,OSAKA 565,JAPAN

来源：

SYNLETT | 1991年 / 12期

关键词：

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-(tert-Butyldimethylsilyl)-alpha-(tributylstannyl)acetic esters 3, prepared in situ by the addition of alkoxytributylstannanes 2 to tert-butyldimethylsilylketene (1), reacted with aldehydes 4 in the presence of titanium(IV) chloride to give beta-hydroxy-alpha-silyl esters 5 with high syn-selectivity in good overall yield. Stereocontrolled elimination of 5 gave possible entry to both (E)- and (Z)-alpha, beta-unsaturated esters 6 depending on conditions used.

引用

页码：911 / 912

页数：2

共 14 条

[1]

Ager D. J., 1990, ORG REACTIONS, V38, P1, DOI DOI 10.1002/0471264180.0R038.01

[2] TRIMETHYLSILYLKETENE - REACTIVITY AND STABILIZATION [J].

ALLEN, AD ;

TIDWELL, TT .

TETRAHEDRON LETTERS, 1991, 32 (07) :847-850

[3] A NEW METHOD FOR GENERATING TRICHLOROTITANIUM(IV) ESTER HOMOENOLATES - DIRECT TIN TITANIUM EXCHANGE [J].

GOSWAMI, R .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5907-5909

[4]

HARTZELL SL, 1974, TETRAHEDRON LETT, P1403

[5] PETERSON OLEFINATION REACTION USING (TRIMETHYLGERMYL)ACETATE - STEREOSELECTIVE SYNTHESIS OF (E)-2-ALKENOIC ACID-ESTERS [J].

INOUE, S ;

SATO, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) :347-352

[6] AN EFFICIENT SYNTHESIS OF ALPHA-SILYLACETATES HAVING VARIOUS TYPES OF FUNCTIONAL-GROUPS IN THE MOLECULES [J].

KITA, Y ;

SEKIHACHI, J ;

HAYASHI, Y ;

DA, YZ ;

YAMAMOTO, M ;

AKAI, S .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (03) :1108-1112

[7]

KITA Y, 1991, SYNLETT, P401

[8]

LARCHEVEQUE M, 1981, J CHEM SOC CHEM COMM, P877, DOI 10.1039/c39810000877

[9] STEREOCONTROLLED SYNTHESIS OF ALPHA,BETA-UNSATURATED CARBOXYLIC ESTERS FROM O-METHYL-C,O-BIS(TRIMETHYLSILYL)KETENE ACETAL AND ALIPHATIC-ALDEHYDES [J].

MATSUDA, I ;

IZUMI, Y .

TETRAHEDRON LETTERS, 1981, 22 (19) :1805-1808

[10]

NIKOLAEVA SN, 1989, ZH OBSHCH KHIM+, V59, P1674

← 1 2 →