A practical one-pot synthesis of vinylstannanes from ketones

被引：10

作者：

Darwish, Alla ^{[1
]}

Chong, J. Michael ^{[1
]}

机构：

[1] Univ Waterloo, Dept Chem, Guelph Waterloo Ctr Grad Work Chem & Biochem, Waterloo, ON N2L 3G1, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 04期

关键词：

D O I：

10.1021/jo062145f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of ketones with Bu3SnLi followed by addition of MsCl/Et3N to the resulting alkoxide provides vinylstannanes. Cyclic vinylstannanes are particularly amenable to this procedure and isolated yields of 81-83% could be consistently attained. Traces of Bu3SnH in crude reaction products could be removed by stirring in CHCl3 with a catalytic amount of AIBN followed by filtration through silica gel.

引用

收藏

页码：1507 / 1509

页数：3

相关论文

共 53 条

[1] PHOTOOXYGENATION OF VINYLSTANNANES - TIN-SUBSTITUTED ALLYLIC HYDROPEROXIDES THROUGH THE REGIOSELECTIVE AND DIASTEREOSELECTIVE ENE REACTION WITH SINGLET OXYGEN [J].

ADAM, W ;

KLUG, P .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (12) :3416-3420

[2] Enantioselective synthesis of the tricyclic core of GKK1032, novel antibiotic anti-tumor agents, by employing an intramolecular Diels-Alder cycloaddition strategy [J].

Asano, M ;

Inoue, M ;

Katoh, T .

SYNLETT, 2005, (10) :1539-1542

[3]

Barbero A, 2001, ANGEW CHEM INT EDIT, V40, P2101, DOI 10.1002/1521-3773(20010601)40:11<2101::AID-ANIE2101>3.0.CO

[4]

2-H

[5] RING-FORMATION FROM ALLYLSTANNANES AND VINYLSTANNANES INITIATED BY TREATMENT WITH BUTYL-LITHIUM [J].

BARBERO, A ;

CUADRADO, P ;

GONZALEZ, AM ;

PULIDO, FJ ;

RUBIO, R ;

FLEMING, I .

TETRAHEDRON LETTERS, 1992, 33 (39) :5841-5842

[6] REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF (E)-2-METHYL-1-ALKENYLTRIMETHYLSTANNANES FROM 1-ALKYNES [J].

BELLINA, F ;

CARPITA, A ;

FONTANA, EA ;

ROSSI, R .

TETRAHEDRON, 1994, 50 (17) :5189-5202

[7] Organoselenium-based entry into versatile, α-(2-tributylstannyl)vinyl amino acids in scalemic form:: A new route to vinyl stannanes [J].

Berkowitz, DB ;

McFadden, JM ;

Chisowa, E ;

Semerad, CL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (44) :11031-11032

[8] Radical hydrostannylation, Pd(0)-catalyzed hydrostannylation, stannylcupration of propargyl alcohols and enynols: Regio- and stereoselectivities [J].

Betzer, JF ;

Delaloge, F ;

Muller, B ;

Pancrazi, A ;

Prunet, J .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) :7768-7780

[9] TOTAL SYNTHESIS OF IONOPHORE ANTIBIOTIC X-14547A (INDANOMYCIN) [J].

BURKE, SD ;

PISCOPIO, AD ;

KORT, ME ;

MATULENKO, MA ;

PARKER, MH ;

ARMISTEAD, DM ;

SHANKARAN, K .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (02) :332-347

[10] Total synthesis of the polyene-polyol macrolide RK-397, featuring cross-couplings of alkynylepoxide modules [J].

Burova, SA ;

McDonald, FE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (08) :2495-2500

← 1 2 3 4 5 6 →