Allene-alkyne cross-coupling for stereoselective synthesis of substituted 1,4-dienes and cross-conjugated trienes

被引:24
作者
Shimp, Heidi L. [1 ]
Hare, Alissa [1 ]
McLaughlin, Martin [1 ]
Micalizio, Glenn C. [1 ]
机构
[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA
关键词
D O I
10.1016/j.tet.2008.02.015
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Titanium-mediated cross-coupling of allenic alcohols with alkynes has been investigated. Divergent reaction pathways were discovered that provide either stereodefined 1,4-dienes or substituted cross-conjugated trienes. In short, allene substitution plays a critical role in the determination of reaction pathway. (c) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3437 / 3445
页数:9
相关论文
共 41 条
[1]   Synthesis of cross-conjugated trienes by dimerization of allenes with palladium-phenol catalyst [J].
Arisawa, M ;
Sugihara, T ;
Yamaguchi, M .
CHEMICAL COMMUNICATIONS, 1998, (23) :2615-2616
[2]   POLYMERS .4. POLYMERIC DIELS-ALDER REACTIONS [J].
BAILEY, WJ ;
ECONOMY, J ;
HERMES, ME .
JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (09) :3295-&
[3]   PYROLYSIS OF ESTERS .3. SYNTHESIS OF 2-VINYLBUTADIENE [J].
BAILEY, WJ ;
ECONOMY, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (05) :1133-1136
[4]   2-VINYL-1,3-BUTADIENE [J].
BLOMQUIST, AT ;
VERDOL, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (01) :81-83
[5]   Cross-coupling for cross-conjugation: Practical synthesis and Diels-Alder reactions of [3]dendralenes [J].
Bradford, Tanya A. ;
Payne, Alan D. ;
Willis, Anthony C. ;
Paddon-Row, Michael N. ;
Sherburn, Michael S. .
ORGANIC LETTERS, 2007, 9 (23) :4861-4864
[6]   Consecutive Rh(I)-catalyzed Alder-ene/Diels-Alder/Diels-Alder reaction sequence affording rapid entry to polycyclic compounds [J].
Brummond, KM ;
You, LF .
TETRAHEDRON, 2005, 61 (26) :6180-6185
[7]   A rhodium(I)-catalyzed formal allenic Alder ene reaction for the rapid and stereoselective assembly of cross-conjugated trienes [J].
Brummond, KM ;
Chen, HF ;
Sill, P ;
You, LF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (51) :15186-15187
[8]   GROUP-4 METAL-COMPLEXES OF BENZYNES, CYCLOALKYNES, ACYCLIC ALKYNES, AND ALKENES [J].
BUCHWALD, SL ;
NIELSEN, RB .
CHEMICAL REVIEWS, 1988, 88 (07) :1047-1058
[9]   USE OF OXO-METALLIC DERIVATIVES IN ISOMERIZATION-REACTIONS OF UNSATURATED ALCOHOLS [J].
CHABARDES, P ;
KUNTZ, E ;
VARAGNAT, J .
TETRAHEDRON, 1977, 33 (14) :1775-1783
[10]  
DOERING WVE, 1963, TETRAHEDRON, V19, P715