Cobalt-catalyzed cycloisomerization of 1,6-enynes and allyl propargyl ethers

被引:35
作者
Ajamian, A [1 ]
Gleason, JL [1 ]
机构
[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada
关键词
D O I
10.1021/ol034541f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
graphic 1,6-Enynes and allyl propargyl ethers undergo a cobalt-catalyzed formal 5-endo-dig cyclization to form vinyl cyclopentenes and dihydrofurans, respectively. The use of equimolar amounts of dicobalt octacarbonyl and trimethyl phosphite affords optimum yields and improved selectivity for cycloisomerization vs alkene isomerization.
引用
收藏
页码:2409 / 2411
页数:3
相关论文
共 27 条
[1]   Diastereoselective synthesis of 2H,5H-dihydrofurans by cobalt-mediated cycloisomerization of allyl propargyl ethers.: Application to poly-THF molecules [J].
Ajamian, A ;
Gleason, JL .
ORGANIC LETTERS, 2001, 3 (26) :4161-4164
[2]   The behavior of 1,n-enynes in the presence of transition metals [J].
Aubert, C ;
Buisine, O ;
Malacria, M .
CHEMICAL REVIEWS, 2002, 102 (03) :813-834
[3]   An allenic Pauson-Khand-type reaction:: A reversal in π-bond selectivity and the formation of seven-membered rings [J].
Brummond, KM ;
Chen, HF ;
Fisher, KD ;
Kerekes, AD ;
Rickards, B ;
Sill, PC ;
Geib, SJ .
ORGANIC LETTERS, 2002, 4 (11) :1931-1934
[4]   New stable catalysts of the Pauson-Khand annelation [J].
Comely, AC ;
Gibson, SE ;
Stevenazzi, A ;
Hales, NJ .
TETRAHEDRON LETTERS, 2001, 42 (06) :1183-1185
[5]   Diastereoselective formation of 5-vinylcyclopentenes from 1,6-enynes: Cobalt-mediated C-H allylic activation and formal 5-endo-dig cyclization [J].
Dolaine, R ;
Gleason, JL .
ORGANIC LETTERS, 2000, 2 (12) :1753-1756
[6]   A stable catalyst of the Pauson-Khand annelation [J].
Gibson, SE ;
Johnstone, C ;
Stevenazzi, A .
TETRAHEDRON, 2002, 58 (24) :4937-4942
[7]   Titanocene-catalyzed cyclocarbonylation of enynes to cyclopentenones [J].
Hicks, FA ;
Kablaoui, NM ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (39) :9450-9451
[8]   Rearrangement of 1-(1-alkynyl)cyclopropanols to 2-cyclopentenones via their hexacarbonyldicobalt complexes.: A new use of alkyne-Co2(CO)6 complexes in organic synthesis [J].
Iwasawa, N ;
Matsuo, T ;
Iwamoto, M ;
Ikeno, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (16) :3903-3914
[9]   Catalytic Pauson-Khand reaction in super critical fluids [J].
Jeong, N ;
Hwang, SH ;
Lee, YW ;
Lim, JS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (43) :10549-10550
[10]   CATALYTIC VERSION OF THE INTRAMOLECULAR PAUSON-KHAND REACTION [J].
JEONG, N ;
HWANG, SH ;
LEE, YS ;
CHUNG, YK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) :3159-3160