Rh(I)-catalyzed intramolecular allenic Pauson-Khand reaction: Construction of a bicyclo[5.3.0]dec-1,7-dien-9-one skeleton

被引:107
作者
Mukai, C [1 ]
Nomura, I [1 ]
Yamanishi, K [1 ]
Hanaoka, M [1 ]
机构
[1] Kanazawa Univ, Fac Pharmaceut Sci, Kanazawa, Ishikawa 9200934, Japan
关键词
D O I
10.1021/ol020051w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] 1-Phenylsulfonylallenes possessing a hexynyl appendage in refluxing toluene in the presence of catalytic amount of rhodium(l) catalyst under a carbon monoxide atmosphere underwent regloselective formal [2 + 2 + 1]-cycloaddition to produce the corresponding bicyclo[5.3.0]dec-1,7-dien-9-one derivatives in acceptable yields.
引用
收藏
页码:1755 / 1758
页数:4
相关论文
共 40 条
[1]   PAUSON-KHAND REACTION WITH ALLENIC COMPOUNDS .1. SYNTHESIS OF 4-ALKYLIDENE-2-CYCLOPENTENONES [J].
AHMAR, M ;
ANTRAS, F ;
CAZES, B .
TETRAHEDRON LETTERS, 1995, 36 (25) :4417-4420
[2]   Pauson-Khand reaction with allenic compounds .2. Reactivity of functionalized allenes. [J].
Ahmar, M ;
Chabanis, O ;
Gauthier, J ;
Cazes, B .
TETRAHEDRON LETTERS, 1997, 38 (30) :5277-5280
[3]   Pauson-Khand cycloaddition of alpha,omega-allenynes. [J].
Ahmar, M ;
Locatelli, C ;
Colombier, D ;
Cazes, B .
TETRAHEDRON LETTERS, 1997, 38 (30) :5281-5284
[4]   Silicon electronic effect in the Pauson-Khand reaction of alkynylsilanes with allenes [J].
Antras, F ;
Ahmar, M ;
Cazes, B .
TETRAHEDRON LETTERS, 2001, 42 (46) :8157-8160
[5]   Regioselectivity in the Pauson-Khand reaction of allenic hydrocarbons [J].
Antras, F ;
Ahmar, M ;
Cazes, B .
TETRAHEDRON LETTERS, 2001, 42 (46) :8153-8156
[6]   Zirconium-mediated intramolecular coupling of terminal alkynes and their subsequent carbonylation: Novel synthesis of seven- and eight-membered heterocycles [J].
Barluenga, J ;
Sanz, R ;
Fananas, FJ .
CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (08) :1324-1336
[7]   Recent advances in the Pauson-Khand reaction and related [2+2+1] cycloadditions [J].
Brummond, KM ;
Kent, JL .
TETRAHEDRON, 2000, 56 (21) :3263-3283
[8]   An intramolecular allenic [2+2+1]cycloaddition [J].
Brummond, KM ;
Wan, HH ;
Kent, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (19) :6535-6545
[9]   The allenic Pauson-Khand cycloaddition.: Dependence in π-bond selectivity on substrate structure. [J].
Brummond, KM ;
Wan, H .
TETRAHEDRON LETTERS, 1998, 39 (09) :931-934
[10]   A short synthesis of the potent antitumor agent (±)-hydroxymethylacylfulvene using an allenic Pauson-Khand type cycloaddition [J].
Brummond, KM ;
Lu, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (21) :5087-5088