Iridium complex-catalyzed reaction of 1,6-enynes: Cycloaddition and cycloisomerization

被引：81

作者：

Kezuka, S ^{[1
]}

Okado, T ^{[1
]}

Niou, E ^{[1
]}

Takeuchi, R ^{[1
]}

机构：

[1] Aoyama Gakuin Univ, Dept Chem & Biol Sci, Sagamihara, Kanagawa 2298558, Japan

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 09期

关键词：

D O I：

10.1021/ol050085e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,6-Enynes reacted with monoynes to give cyclohexadiene derivatives in the presence of a catalytic amount of (Ir(cod)CI](2)/ligand. DPPE was most suitable for cycloaddition. Diastereoselective cycloaddition was also possible. In the absence of monoynes, 1,6-enynes cycloisomerized to (2)-1-alkylidene-2-methylenecyclopentane derivatives. DPPF was most suitable for cyclolsomerization. These results are the first examples of highly Z-selective cycloisomerization.

引用

页码：1711 / 1714

页数：4

共 59 条

[1] Cobalt-catalyzed cycloisomerization of 1,6-enynes and allyl propargyl ethers [J].

Ajamian, A ;

Gleason, JL .

ORGANIC LETTERS, 2003, 5 (14) :2409-2411

[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]

BLANCOURGOITI J, 2004, CHEM SOC REV, V33, P32, DOI DOI 10.1039/B300976A

[4]

Buisine O, 2001, CHEM-EUR J, V7, P3517, DOI 10.1002/1521-3765(20010817)7:16<3517::AID-CHEM3517>3.0.CO

[5]

2-V

[6] Rh-catalyzed enyne cycloisomerization [J].

Cao, P ;

Wang, B ;

Zhang, XM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (27) :6490-6491

[7]

Cao P, 2000, ANGEW CHEM INT EDIT, V39, P4104, DOI 10.1002/1521-3773(20001117)39:22<4104::AID-ANIE4104>3.0.CO

[8]

2-X

[9] INTERMOLECULAR COBALT-MEDIATED [2+2+2]CYCLOADDITIONS - REGIOSPECIFIC ONE-STEP CONSTRUCTION OF BICYCLIC DIENES FROM ALPHA,OMEGA-ENYNES AND ALKYNES [J].

CHANG, CA ;

KING, JA ;

VOLLHARDT, KPC .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (02) :53-55

[10] Iridium(I)-catalyzed cycloisomerization of enynes [J].

Chatani, N ;

Inoue, H ;

Morimoto, T ;

Muto, T ;

Murai, S .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (12) :4433-4436

← 1 2 3 4 5 6 →