Regiospecific and stereoselective synthesis of functionalized and differently metalated alkenes by silyl- or stannylcupration of metalated acetylenes

被引：17

作者：

Cuadrado, P ^{[1
]}

González-Nogal, AM ^{[1
]}

Sánchez, A ^{[1
]}

机构：

[1] Univ Valladolid, Dept Quim Organ, E-47011 Valladolid, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 06期

关键词：

D O I：

10.1021/jo0010983

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Differently metalated vinylcuprate intermediates resulting from silyl- or stannylcupration of silyl- and tin-containing acetylenes reacted with a range of electrophiles, including chlorosilanes and chlorostannanes, affording regio- and stereodefined differently metalated vie and gem silyl- and tin-trisubstituted alkenes, Some of these functionalized polymetalated olefins are interesting synthons in organic chemistry.

引用

页码：1961 / 1965

页数：5

共 15 条

[1] SYNTHESIS OF VINYLSILANES BY SILYL-CUPRATION OF ACETYLENES USING TERT-BUTYLDIPHENYLSILYL-CUPRATE REAGENTS [J].

BARBERO, A ;

CUADRADO, P ;

FLEMING, I ;

GONZALEZ, AM ;

PULIDO, FJ ;

SANCHEZ, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (12) :1525-1532

[2] STANNYL-CUPRATION OF ACETYLENES AND THE REACTION OF THE INTERMEDIATE CUPRATES WITH ELECTROPHILES AS A SYNTHESIS OF SUBSTITUTED VINYLSTANNANES [J].

BARBERO, A ;

CUADRADO, P ;

FLEMING, I ;

GONZALEZ, AM ;

PULIDO, FJ ;

RUBIO, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (14) :1657-1662

[3] THE STANNYL CUPRATION OF ACETYLENES AND THE REACTION OF THE INTERMEDIATE CUPRATES WITH ELECTROPHILES AS A SYNTHESIS OF SUBSTITUTED VINYLSTANNANES [J].

BARBERO, A ;

CUADRADO, P ;

FLEMING, I ;

GONZALEZ, AM ;

PULIDO, FJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (04) :351-353

[4] SYNTHESIS OF ALKENES FROM CARBONYL-COMPOUNDS AND CARBANIONS-ALPHA TO SILICON .6. SYNTHESIS OF TERMINAL ALLENES AND ALLYL CHLORIDES [J].

CHAN, TH ;

MYCHAJLOWSKIJ, W ;

ONG, BS ;

HARPP, DN .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (08) :1526-1532

[5] 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

[6]

Colvin E. W., 1981, SILICON ORGANIC SYNT, P165

[7] THE SYNTHESIS OF 3-TRIMETHYLSILYL-4-DIMETHYL(PHENYL)SILYLBUT-3-EN-2-ONE, A BETA-FUNCTIONALIZED MICHAEL ACCEPTOR [J].

FLEMING, I ;

NEWTON, TW ;

SABIN, V ;

ZAMMATTIO, F .

TETRAHEDRON, 1992, 48 (37) :7793-7802

[8] THE SILYLCUPRATION OF ACETYLENES - A SYNTHESIS OF VINYLSILANES [J].

FLEMING, I ;

NEWTON, TW ;

ROESSLER, F .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (09) :2527-2532

[9] 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

[10] SILICON-DIRECTED NAZAROV REACTIONS .3. STEREOCHEMICAL AND MECHANISTIC CONSIDERATIONS [J].

JONES, TK ;

DENMARK, SE .

HELVETICA CHIMICA ACTA, 1983, 66 (08) :2397-2411

← 1 2 →