Radical hydrostannylation, Pd(0)-catalyzed hydrostannylation, stannylcupration of propargyl alcohols and enynols: Regio- and stereoselectivities

被引：196

作者：

Betzer, JF ^{[1
]}

Delaloge, F ^{[1
]}

Muller, B ^{[1
]}

Pancrazi, A ^{[1
]}

Prunet, J ^{[1
]}

机构：

[1] ECOLE POLYTECH,CNRS,SYNTH ORGAN LAB,DCSO,F-91128 PALAISEAU,FRANCE

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 22期

关键词：

D O I：

10.1021/jo9710339

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Different enynols and propargyl derivatives were sumitted to radical hydrostannylation (Bu3SnH/AIBN), Pd(0)-catalyzed hydrostannylation [Bu3SnH/Pd(0)], and stannylcupration [Bu3Sn(R)CuCNLi2] conditions. Except for the radical stannylation reaction, high regio-and stereoselective formation of vinyl-and dienylstannanes are obtained. Results are tentatively explained in terms of steric Interactions between the alkyne or enyne substituents and the palladium or cuprate moieties in the different reaction intermediates.

引用

页码：7768 / 7780

页数：13

共 49 条

[1] STANNYLMETALLATION OF CONJUGATED ENYNES
AKSELA, R
OEHLSCHLAGER, AC
[J]. TETRAHEDRON, 1991, 47 (07) : 1163 - 1176
[2] Alami M, 1996, SYNLETT, P755
[3] [Anonymous], 1978, ORGANOMETALLIC MECHA
[4] ARDISSON J, 1992, B SOC CHIM FR, V129, P401
[5] LEWIS-ACID CATALYZED TRANS-HYDROSTANNYLATION OF ACETYLENES
ASAO, N
LIU, JX
SUDOH, T
YAMAMOTO, Y
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (23) : 2405 - 2406
[6] STANNYL-CUPRATION OF ACETYLENES AND THE REACTION OF THE INTERMEDIATE CUPRATES WITH ELECTROPHILES AS A SYNTHESIS OF SUBSTITUTED VINYLSTANNANES
BARBERO, A
CUADRADO, P
FLEMING, I
GONZALEZ, AM
PULIDO, FJ
RUBIO, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (14): : 1657 - 1662
[7] THE STANNYL CUPRATION OF ACETYLENES AND THE REACTION OF THE INTERMEDIATE CUPRATES WITH ELECTROPHILES AS A SYNTHESIS OF SUBSTITUTED VINYLSTANNANES
BARBERO, A
CUADRADO, P
FLEMING, I
GONZALEZ, AM
PULIDO, FJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (04) : 351 - 353
[8] STEREOCONTROLLED SYNTHESIS OF CALYCULIN-A - CONSTRUCTION OF THE C(1)-C(14) TETRAENE NITRILE UNIT
BARRETT, AGM
EDMUNDS, JJ
HENDRIX, JA
HORITA, K
PARKINSON, CJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (17) : 1238 - 1240
[9] C-5-BRANCHED VINYLTIN ACETALS AS VERSATILE TOOLS FOR TERPENIC SYNTHESIS
BEAUDET, I
LAUNAY, V
PARRAIN, JL
QUINTARD, JP
[J]. TETRAHEDRON LETTERS, 1995, 36 (03) : 389 - 392
[10] INSITU CUPRATE FORMATION VIA TRANSMETALATION BETWEEN VINYLSTANNANES AND HIGHER-ORDER CYANOCUPRATES
BEHLING, JR
BABIAK, KA
NG, JS
CAMPBELL, AL
MORETTI, R
KOERNER, M
LIPSHUTZ, BH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (08) : 2641 - 2643

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