REGIOCONTROLLED AND STEREOCONTROLLED STANNYLMETALLATION OF 3,3-DIETHOXY-PROP-1-YNE AND 4,4-DIETHOXY-BUT-1-YNE - AN EFFICIENT ACCESS TO THE CORRESPONDING VINYLTINS WITH FIXED CONFIGURATIONS

被引：61

作者：

BEAUDET, I ^{[1
]}

PARRAIN, JL ^{[1
]}

QUINTARD, JP ^{[1
]}

机构：

[1] FAC SCI & TECH NANTES,SYNTHESE ORGAN LAB,CNRS,URA 475,2 RUE HOUSSINIERE,F-44072 NANTES 03,FRANCE

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 44期

关键词：

STANNYLMETALLATION; ALKYNES; VINYLTINS; (E)-BETA-FORMYLVINYLANION EQUIVALENT; (E)-BETA-(FORMYLMETHYL)VINYLANION EQUIVALENT;

D O I：

10.1016/0040-4039(91)80162-Y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stannylmetallation of propargyl or homopropargyl acetals has been exploited to obtain the corresponding vinyltin as a single geometrical isomer, result of a cis-addition on the triple bond.

引用

页码：6333 / 6336

页数：4

共 20 条

[1] ALKENYL COPPER REAGENTS .18. CARBOCUPRATION OF ACETYLENIC ACETALS AND KETALS SYNTHESIS OF MANICONE, GERANIAL AND 2,4 (E,Z)-DIENALS [J].

ALEXAKIS, A ;

COMMERCON, A ;

COULENTIANOS, C ;

NORMANT, JF .

TETRAHEDRON, 1984, 40 (04) :715-731

[2] SILYLSTANNANES IN ORGANIC-SYNTHESIS - SCOPE AND LIMITATION OF PALLADIUM-CATALYZED REACTION WITH ACETYLENES [J].

CHENARD, BL ;

VANZYL, CM .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (19) :3561-3566

[3] SPECTROSCOPIC AND CHEMICAL EVIDENCE FOR THE REVERSIBLE FORMATION OF VINYLCOPPER INTERMEDIATES IN THE STANNYLCUPRATION OF TERMINAL ALKYNES [J].

HUTZINGER, MW ;

SINGER, RD ;

OEHLSCHLAGER, AC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (25) :9397-9398

[4] FORMATION OF ORGANOTIN COMPOUNDS WITH SN-MG BONDS [J].

LAHOURNERE, JC ;

VALADE, J .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1970, 22 (01) :C3-+

[5] TRANSMETALATION REACTIONS OF HIGHER-ORDER CYANOCUPRATES - DIRECT FORMATION OF TRIALKYLTIN CUPRATES FROM TIN HYDRIDES WHICH BYPASSES ORGANO-LITHIUM INTERMEDIATES [J].

LIPSHUTZ, BH ;

ELLSWORTH, EL ;

DIMOCK, SH ;

REUTER, DC .

TETRAHEDRON LETTERS, 1989, 30 (16) :2065-2068

[6] REGIO-SELECTIVE AND STEREO-SELECTIVE SYNTHESIS OF VINYLSTANNANES - TRANSITION-METAL CATALYZED STANNYLMETALATION OF ACETYLENES AND CONVERSION OF ENOL TRIFLATES AND VINYL IODIDES INTO VINYLSTANNANES [J].

MATSUBARA, S ;

HIBINO, JI ;

MORIZAWA, Y ;

OSHIMA, K ;

NOZAKI, H .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 285 (1-3) :163-172

[7] FORMATION AND REACTIONS OF OLEFINS WITH VICINAL SILYL AND STANNYL SUBSTITUENTS [J].

MITCHELL, TN ;

WICKENKAMP, R ;

AMAMRIA, A ;

DICKE, R ;

SCHNEIDER, U .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22) :4868-4874

[8] PALLADIUM CATALYSIS IN ORGANOTIN CHEMISTRY - ADDITION OF HEXAALKYLDITINS TO ALKYNES [J].

MITCHELL, TN ;

AMAMRIA, A ;

KILLING, H ;

RUTSCHOW, D .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 304 (1-2) :257-265

[9]

MITCHELL TN, 1989, MAIN GROUP MET CHEM, V12, P425

[10]

NORMANT JF, 1981, SYNTHESIS-STUTTGART, P841

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