The regio- and stereochemical course of reductive cross-coupling reactions between 1,3-disubstituted allenes and vinylsilanes: synthesis of (Z)-dienes

被引：6

作者：

Barlan, Allan U. ^{[1
]}

Micalizio, Glenn C. ^{[1
]}

机构：

[1] Scripps Florida, Scripps Res Inst, Dept Chem, Jupiter, FL 33458 USA

来源：

TETRAHEDRON | 2010年 / 66卷 / 26期

基金：

美国国家卫生研究院;

关键词：

Allenes; Titanium; Reductive Cross-Coupling; Z-dienes; BOND-FORMING HYDROGENATION; ALPHA-HYDROXY ESTERS; ALLYLIC ALCOHOLS; STEREOSELECTIVE-SYNTHESIS; ETHYLMAGNESIUM BROMIDE; IMINE VINYLATION; CATALYZED HOMOALLYLATION; SUBSTITUTED 1,4-DIENES; 3+2 CYCLOADDITION; TERMINAL ALLENES;

D O I：

10.1016/j.tet.2010.02.062

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In investigations aimed at exploring the potential of disubstituted allenes in stereoselective synthesis, we report studies that explore the reductive cross-coupling reaction of vinylsilanes with a range of substituted allenes. Regiochemical control is attained by employing allenic alkoxides, where the proximal heteroatom dictates the site-selectivity in a process that proceeds by net formal metallo-[3,3] rearrangement (directed carbometalation/elimination). Stereoselectivity in these reactions is complex, with both the nature of allene substitution and relative stereochemistry of the substrate impacting the stereoselective generation of each alkene of a substituted 1,3-diene. (C) 2010 Published by Elsevier Ltd.

引用

页码：4775 / 4783

页数：9

共 100 条

[1] Formation and Utility of Azasilacyclopentadienes Derived from Silacyclopropenes and Nitriles [J].

Anderson, Laura L. ;

Woerpel, K. A. .

ORGANIC LETTERS, 2009, 11 (02) :425-428

[2]

Arimoto H, 1998, SYNLETT, P765

[3] Studies in macrolide antibiotic synthesis: The role of tethered alkoxides in titanium alkoxide-mediated regioselective reductive coupling reactions [J].

Bahadoor, AB ;

Micalizio, GC .

ORGANIC LETTERS, 2006, 8 (06) :1181-1184

[4] A pentenyl dianion-based strategy for convergent synthesis of ene-1,5-diols [J].

Bahadoor, AB ;

Flyer, A ;

Micalizio, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (11) :3694-3695

[5] Allylic amines via iridium-catalyzed C-C bond forming hydrogenation: Imine vinylation in the absence of stoichiometric byproducts or metallic reagents [J].

Barchuk, Andriy ;

Ngai, Ming-Yu ;

Krische, Michael J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (27) :8432-+

[6] Dehydrogenative cyclocondensation of aldehydes, alkynes, and dialkylsilanes [J].

Baxter, Ryan D. ;

Montgomery, John .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (30) :9662-+

[7] Conversion of Allylic Alcohols to Stereodefined Trisubstituted Alkenes: A Complementary Process to the Claisen Rearrangement [J].

Belardi, Justin K. ;

Micalizio, Glenn C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (50) :16870-+

[8] Intermolecular Silacarbonyl Ylide Cycloadditions: A Direct Pathway to Oxasilacyclopentenes [J].

Bourque, Laura E. ;

Woerpel, K. A. .

ORGANIC LETTERS, 2008, 10 (22) :5257-5260

[9] Cobalt-catalyzed reductive coupling of activated alkenes with alkynes [J].

Chang, Hong-Tai ;

Jayanth, Thiruvellore Thatai ;

Wang, Chun-Chih ;

Cheng, Chien-Hong .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (39) :12032-12041

[10] Cobalt-catalyzed diastereoselective reductive [3+2] cycloaddition of allenes and enones [J].

Chang, Hong-Tai ;

Jayanth, Thiruvellore Thatai ;

Cheng, Chien-Hong .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (14) :4166-+

← 1 2 3 4 5 6 7 8 9 10 →