A convenient synthesis of protected and free homoallylic alcohols: Catalytic use of dibutyltin dichloride in the allylation of aldehydes with allyltributyltin

被引：11

作者：

Whitesell, JK

Apodaca, R

机构：

[1] Dept. of Chemistry and Biochemistry, University Texas at Austin, Austin

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 23期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/0040-4039(96)00719-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new procedure for the allylation of aldehydes with allyltributyltin in the presence of 10 mol% dibutyltin dichloride and either an acid chloride or trimethylsilyl chloride has been developed. Homoallylic esters, carbonates, trimethylsilyl ethers, and alcohols were obtained in up to 99% yield. (C) 1996 Elsevier Science Ltd

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页码：3955 / 3958

页数：4

相关论文

共 21 条

[1] ENANTIOSELECTIVE AND DIASTEREOSELECTIVE CATALYSIS OF ADDITION-REACTION OF ALLYLIC SILANES AND STANNANES TO GLYOXYLATES BY BINAPHTHOL-DERIVED TITANIUM COMPLEX [J].

AOKI, S ;

MIKAMI, K ;

TERADA, M ;

NAKAI, T .

TETRAHEDRON, 1993, 49 (09) :1783-1792

[2] YTTERBIUM TRIFLUOROMETHANESULFONATE [YB(OTF)(3)] AS A NOVEL CATALYST FOR THE ALLYLATION OF ALDEHYDES [J].

ASPINALL, HC ;

BROWNING, AF ;

GREEVES, N ;

RAVENSCROFT, P .

TETRAHEDRON LETTERS, 1994, 35 (26) :4639-4640

[3] ALLYLSTANNATION .7. PREPARATION OF CARBOXYLIC-ACID 1-ALKENE-4-YL AND 1-ALKYNE-4-YL ESTERS BY TRANSALKOXYLATION OF 4-NORMAL-DIBUTYLCHLOROSTANNOXY-1-ALKENES AND 4-NORMAL-DIBUTYLCHLOROSTANNOXY-1-ALKYNES WITH ACYL CHLORIDES [J].

BOARETTO, A ;

MARTON, D ;

TAGLIAVINI, G .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 288 (03) :283-287

[4] CATALYTIC ASYMMETRIC-SYNTHESIS OF HOMOALLYLIC ALCOHOLS [J].

COSTA, AL ;

PIAZZA, MG ;

TAGLIAVINI, E ;

TROMBINI, C ;

UMANIRONCHI, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :7001-7002

[5]

COZZI PG, 1994, SYNLETT, P857

[6] ALLYLBUTYLTIN HALIDES (CH2=CHCH2)SNBU3-NCLN(N=0,1,2,3) - PREPARATION, C-13 NMR CHARACTERIZATION AND ALLYLSTANNYLATION ABILITY TOWARDS KETONES AND ALDEHYDES [J].

GAMBARO, A ;

PERUZZO, V ;

PLAZZOGNA, G ;

TAGLIAVINI, G .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1980, 197 (01) :45-50

[7] AQUEOUS REACTIONS WITH A LEWIS-ACID AND AN ORGANOMETALLIC REAGENT - THE SCANDIUM TRIFLUOROMETHANESULFONATE-CATALYZED ALLYLATION REACTION OF CARBONYL-COMPOUNDS WITH TETRAALLYLTIN [J].

HACHIYA, I ;

KOBAYASHI, S .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25) :6958-6960

[8] CATALYTIC ASYMMETRIC ALLYLATION (CAA) REACTIONS .2. A NEW ENANTIOSELECTIVE ALLYLATION PROCEDURE [J].

KECK, GE ;

GERACI, LS .

TETRAHEDRON LETTERS, 1993, 34 (49) :7827-7828

[9] KINETICALLY CONTROLLED REGIOSPECIFIC SILYLATION OF POLYOLS VIA DIBUTYLSTANNANEDIYL ACETALS [J].

LEIGH, DA ;

MARTIN, RP ;

SMART, JP ;

TRUSCELLO, AM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (11) :1373-1374

[10] Chiral allylic and allenic stannanes as reagents for asymmetric synthesis [J].

Marshall, JA .

CHEMICAL REVIEWS, 1996, 96 (01) :31-47