Ruthenium-Catalyzed Homo Diels-Alder [2+2+2] Cycloadditions of Alkynyl Phosphonates with Bicyclo[2.2.1]hepta-2,5-diene

被引：23
作者：
Kettles, Tanner J. [1 ]
Cockburn, Neil [1 ]
Tam, William [1 ]
机构：
[1] Univ Guelph, Dept Chem, Guelph Waterloo Ctr Grad Work Chem & Biochem, Guelph, ON N1G 2W1, Canada
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 16期
基金：
加拿大自然科学与工程研究理事会;
关键词：
BICYCLIC ALKENES; ASYMMETRIC INDUCTION; ACID-DERIVATIVES; NORBORNADIENES; CYCLOADDUCTS; REACTIVITY; COMPONENT; TRIQUINANES; NORBORNENES; DIQUINANES;
D O I：
10.1021/jo2010928
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Ruthenium-catalyzed homo Diels-Alder [2 + 2 + 2] cycloadditions between alkynyl phosphonates and bicyclo[2.2.1]hepta-2,5-diene were studied. The observed reactivity was found to be dependent on the presence of the phosphonate moiety. The Ru-catalyzed cycloaddition was compatible with a variety of aromatic and aliphatic substituted alkynyl phosphonates, providing the corresponding phosphonate substituted delta-cyclenes in low to good yields (up to 88%).
引用
收藏
页码：6951 / 6957
页数：7
相关论文
共 49 条
[1]   Alkynyl halides in ruthenium(II)-catalyzed [2+2] cycloadditions of bicyclic alkenes [J].
Allen, Anna ;
Villeneuve, Karine ;
Cockburn, Neil ;
Fatila, Elisabeth ;
Riddell, Nicole ;
Tam, William .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (24) :4178-4192
[2]   DELTACYCLENE FORMATION CATALYZED BY CATIONIC CO(II) COMPLEXES [J].
BINGER, P ;
ALBUS, S .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 493 (1-2) :C6-C8
[3]   Study on the reactivity of oxabicyclic Alkenes in ruthenium-catalyzed [2+2] cycloadditions [J].
Burton, Ryan R. ;
Tam, William .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (19) :7333-7336
[4]   Ruthenium-catalyzed [2+2] cycloadditions between C1-substituted 7-oxanorbornadienes and alkynes [J].
Burton, Ryan R. ;
Tam, William .
TETRAHEDRON LETTERS, 2006, 47 (40) :7185-7189
[5]   Opening norbornadiene homo Diels-Alder adducts to bicyclic systems [J].
Chen, Y ;
Snyder, JK .
TETRAHEDRON LETTERS, 1997, 38 (09) :1477-1480
[6]   Opening the [4+2+2] cycloadducts of bicyclo[2.2.1]hepta-2,5-dienes (norbornadienes) to cis-fused bicyclo[5.3.0]decanes [J].
Chen, Y ;
Snyder, JK .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (21) :6943-6957
[7]   Metal-catalyzed [4+2+2] cycloadditions: Cycloadducts of substituted norbornadienes and their opening with Zeise's dimer [J].
Chen, Y ;
Snyder, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (07) :2060-2061
[8]   Ruthenium-Catalyzed [2+2] Cycloadditions of Bicyclic Alkenes with Alkynyl Phosphonates [J].
Cockburn, Neil ;
Karimi, Elham ;
Tam, William .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) :5762-5765
[9]   NOVEL ACYCLONUCLEOTIDES - SYNTHESIS AND ANTIVIRAL ACTIVITY OF ALKENYLPHOSPHONIC ACID-DERIVATIVES OF PURINES AND A PYRIMIDINE [J].
HARNDEN, MR ;
PARKIN, A ;
PARRATT, MJ ;
PERKINS, RM .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (10) :1343-1355
[10]   An improved cobalt catalyst for homo Diels-Alder reactions of acyclic 1,3-dienes with alkynes [J].
Hilt, G ;
du Mesnil, FX .
TETRAHEDRON LETTERS, 2000, 41 (35) :6757-6761
12345