Iridium complex-catalyzed enantioselective intramolecular [4+2] cycloaddition of dieneynes

被引：39

作者：

Shibata, T ^{[1
]}

Takasaku, K ^{[1
]}

Takesue, Y ^{[1
]}

Hirata, N ^{[1
]}

Takagi, K ^{[1
]}

机构：

[1] Okayama Univ, Fac Sci, Dept Chem, Okayama 7008530, Japan

来源：

SYNLETT | 2002年 / 10期

关键词：

catalysis; chiral auxiliaries; cycloadditions; Diels-Alder reactions; iridium;

D O I：

10.1055/s-2002-34217

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalytic and highly enantioselective intramolecular [4+2] cycloaddition of dieneynes was achieved by use of chiral iridium complex prepared in situ from [IrCl(cod)](2) and BDPP [2,4-bis(diphenylphosphino)pentane]. The reaction proceeded in refluxed tent-butyl acetate to give chiral cyclohexa-1,4-dienes in very high enantiomeric excess.

引用

页码：1681 / 1682

页数：2

共 20 条

[1] Asymmetric Diels-Alder reactions catalyzed by a triflic acid activated chiral oxazaborolidine [J].

Corey, EJ ;

Shibata, T ;

Lee, TW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (15) :3808-3809

[2]

Evans D. A., 1999, COMPREHENSIVE ASYMME, V3, P1177

[3] Rhodium-catalyzed asymmetric [4+2] cycloisomerization reactions [J].

Gilbertson, SR ;

Hoge, GS ;

Genov, DG .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :10077-10080

[4] Rhodium catalyzed intramolecular [4+2] cycloisomerization reactions [J].

Gilbertson, SR ;

Hoge, GS .

TETRAHEDRON LETTERS, 1998, 39 (15) :2075-2078

[5]

Heath H, 2001, SYNTHESIS-STUTTGART, P2341

[6] NOVEL CYCLIZATION REACTIONS ON TRANSITION-METAL TEMPLATES - THE CATALYSIS OF INTRAMOLECULAR [4 + 2] CYCLOADDITIONS BY LOW VALENT RHODIUM COMPLEXES [J].

JOLLY, RS ;

LUEDTKE, G ;

SHEEHAN, D ;

LIVINGHOUSE, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (12) :4965-4966

[7] Transition metal-mediated cycloaddition reactions [J].

Lautens, M ;

Klute, W ;

Tam, W .

CHEMICAL REVIEWS, 1996, 96 (01) :49-92

[8] PALLADIUM-CATALYZED TANDEM CARBONYLATION AND INTRAMOLECULAR DIELS-ALDER REACTION OF 4-ALKEN-2-YNYL CARBONATES - A NEW SYNTHETIC METHOD FOR POLYCYCLIC COMPOUNDS [J].

MANDAI, T ;

SUZUKI, S ;

IKAWA, A ;

MURAKAMI, T ;

KAWADA, M ;

TSUJI, J .

TETRAHEDRON LETTERS, 1991, 32 (52) :7687-7688

[9]

Maruoka K., 2000, CATALYTIC ASYMMETRIC, P467

[10] ON THE ASYMMETRIC RH(I) CATALYZED [4+2] CYCLOISOMERIZATION REACTION - ELECTRONIC AND TORSIONAL LIGAND CONTROL OF ABSOLUTE STEREOSELECTION [J].

MCKINSTRY, L ;

LIVINGHOUSE, T .

TETRAHEDRON, 1994, 50 (21) :6145-6154

← 1 2 →