ALPHA-TRIBUTYLSTANNYLACETALS - PREPARATION VIA TRANSACETALIZATION OF DIETHOXYMETHYLTRIBUTYLTIN, AND USE FOR THE SYNTHESIS OF NEW ALPHA-STANNYLATED ETHERS

被引：10

作者：

DUCHENE, A ^{[1
]}

BOISSIERE, S ^{[1
]}

PARRAIN, JL ^{[1
]}

QUINTARD, JP ^{[1
]}

机构：

[1] FAC SCI & TECHN NANTES,SYNTHESE ORGAN SELECT & MAT LAB,CNRS,URA 475,F-44072 NANTES 03,FRANCE

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 1990年 / 387卷 / 02期

关键词：

D O I：

10.1016/0022-328X(90)80020-Z

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The transacetalisation of readily available diethoxymethyltributyltin affords a large variety of new α-stannylacetals, which are expected to have a high potential for selective organic synthesis when they contain labile or chiral alkoxy groups. The α-stannylacetals can be converted into the corresponding substituted α-stannyl-ethers by treatment with organoaluminium halides or by use of an acetyl chloride/Grignard reagent sequence. The study has concentrated on allylic, homoallylic, and homopropargylic derivatives, which offer the best potential for organic synthesis. © 1990.

引用

页码：153 / 162

页数：10

共 23 条

[1]

BARBOT F, 1984, B SOC CHIM FR II-CH, P83

[2]

BARBOT F, 1981, J CHEM RES M, P4016

[3] ALPHA-ALKOXYTIN COMPOUNDS IN ORGANIC-SYNTHESIS - AN EFFICIENT SYNTHESIS OF ALPHA-ETHOXYALKENYL-TIN AND ALPHA-ETHOXYALKYNYL-TIN COMPOUNDS [J].

DUCHENE, A ;

QUINTARD, JP .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (01) :29-30

[4]

DUCHENE A, 1988, THESIS BORDEAUX, pCH2

[5]

ELIEL EL, 1978, J AM CHEM SOC, V100, P1614, DOI 10.1021/ja00473a055

[6]

Hase T. A., 1981, ALDRICHIM ACTA, V14, P73

[7] ASYMMETRIC DIHYDROXYLATION VIA LIGAND-ACCELERATED CATALYSIS [J].

JACOBSEN, EN ;

MARKO, I ;

MUNGALL, WS ;

SCHRODER, G ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (06) :1968-1970

[8] A NEW PREPARATION OF HEXAALKYLDITINS - SN-119 NMR AND CHROMATOGRAPHIC DATA ON LINEAR POLYTINS [J].

JOUSSEAUME, B ;

CHANSON, E ;

BEVILACQUA, M ;

SAUX, A ;

PEREYRE, M ;

BARBE, B ;

PETRAUD, M .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 294 (03) :C41-C45

[9] ISOTOPE-EXCHANGE STUDIES WITH DIETHYL ACETALS IN ETHANOL AND THEIR MECHANISTIC IMPLICATIONS TO PROTOLYTIC REACTIONS OF ACETALS AND VINYL ETHERS [J].

KANKAANP.A ;

SALOMAA, P ;

JUHALA, P ;

AALTONEN, R ;

MATTSEN, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (11) :3618-3624

[10] SE' ADDITION OF HOMOCHIRAL ALPHA-ALKOXYALLYLSTANNANES TO ALDEHYDES [J].

MARSHALL, JA ;

GUNG, WY .

TETRAHEDRON, 1989, 45 (04) :1043-1052

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