Iridium complex-catalyzed Pauson-Khand-type reaction of allenynes

被引：47

作者：

Shibata, T ^{[1
]}

Kadowaki, S ^{[1
]}

Hirase, M ^{[1
]}

Takagi, K ^{[1
]}

机构：

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

来源：

SYNLETT | 2003年 / 04期

关键词：

alkynes; allenes; carbonylations; iridium; Pauson-Khand reaction;

D O I：

10.1055/s-2003-37532

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Vaska's complex [IrCl(CO)(PPh3)(2)] efficiently catalyzes the intramolecular carbonylative [2+2+1] cycloaddition of allenynes. A dimethyl substituent on the allene terminus and a low partial pressure of carbon monoxide realize the selective engagement of the internal it-bond of allene.

引用

页码：573 / 575

页数：3

共 33 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 cycloaddition of alpha,omega-allenynes. [J].

Ahmar, M ;

Locatelli, C ;

Colombier, D ;

Cazes, B .

TETRAHEDRON LETTERS, 1997, 38 (30) :5281-5284

[3] Regioselectivity in the Pauson-Khand reaction of allenic hydrocarbons [J].

Antras, F ;

Ahmar, M ;

Cazes, B .

TETRAHEDRON LETTERS, 2001, 42 (46) :8153-8156

[4] ORGANIC SYNTHESES VIA TRANSITION-METAL COMPLEXES .19. BETA-METHYLENECYCLOPENTENONES VIA IRON CARBONYL-INDUCED [2 + 2 + 1] CYCLOADDITION OF ALKYNES TO ALLENES AND CARBON-MONOXIDE [J].

AUMANN, R ;

WEIDENHAUPT, HJ .

CHEMISCHE BERICHTE-RECUEIL, 1987, 120 (01) :23-27

[5] A rhodium(I)-catalyzed formal allenic Alder ene reaction for the rapid and stereoselective assembly of cross-conjugated trienes [J].

Brummond, KM ;

Chen, HF ;

Sill, P ;

You, LF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (51) :15186-15187

[6] Chiral nonracemic α-alkylidene and α-silylidene cyclopentenones from chiral allenes using an intramolecular allenic Pauson-Khand-type cycloaddition [J].

Brummond, KM ;

Kerekes, AD ;

Wan, HH .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (15) :5156-5163

[7] 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

[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]

Chung YK, 1999, COORDIN CHEM REV, V188, P297

[10] New stable catalysts of the Pauson-Khand annelation [J].

Comely, AC ;

Gibson, SE ;

Stevenazzi, A ;

Hales, NJ .

TETRAHEDRON LETTERS, 2001, 42 (06) :1183-1185

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