Scope of the intramolecular imidotitanium-alkyne [2+2] cycloaddition azatitanetine acylation sequence. An efficient procedure for the synthesis of 2-(2-keto-1-alkylidene)tetrahydropyrrole and related compounds

被引：55

作者：

Fairfax, D ^{[1
]}

Stein, M ^{[1
]}

Livinghouse, T ^{[1
]}

Jensen, M ^{[1
]}

机构：

[1] MONTANA STATE UNIV,DEPT CHEM & BIOCHEM,BOZEMAN,MT 59717

来源：

ORGANOMETALLICS | 1997年 / 16卷 / 08期

关键词：

D O I：

10.1021/om961074f

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Sequential [2 + 2] cycloaddition of transient imidotitanium complexes to tethered alkynes followed by C-acylation of the resulting azatitanetines with acyl cyanides has been shown to provide a range of functionalized tetrahydropyrroles and related derivatives in good to excellent yields. The selectivity of product formation is correlated to the pattern of alkyne substitution.

引用

页码：1523 / 1525

页数：3

共 16 条

[1] [2+2+2]CYCLOADDITIONS OF ALKYNES TO FURANS AND THIOPHENES - A COBALT-MEDIATED ENOL ETHER WALK
BOESE, R
HARVEY, DF
MALASKA, MJ
VOLLHARDT, KPC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (24) : 11153 - 11154
[2] REACTIONS OF TRIMETHYLSILYLCYCLOPENTADIENE DERIVATIVES WITH TITANIUM, NIOBIUM, AND TANTALUM HALIDES
CARDOSO, AM
CLARK, RJH
MOORHOUSE, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1980, (07): : 1156 - 1160
[3] A NOVEL INTRAMOLECULAR CYCLIZATION OF TITANOCENE VINYLIDENE COMPLEXES - FORMATION OF BICYCLIC TITANACYCLO-BUTANES AND TITANACYCLO-BUTENES
DENNEHY, RD
WHITBY, RJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (15) : 1060 - 1062
[4] JENSEN MD, 1991, THESIS U MINNESOTA M
[5] Organolanthanide-catalyzed intramolecular hydroamination/cyclization of aminoalkynes
Li, YW
Marks, TJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (39) : 9295 - 9306
[6] CATALYTIC CU(I) ASSISTED POLYFUNCTIONALIZATION OF ZIRCONACYCLOPENTENES
LIPSHUTZ, BH
SEGI, M
[J]. TETRAHEDRON, 1995, 51 (15) : 4407 - 4420
[7] RAPID AND EFFICIENT PROCEDURES FOR THE SYNTHESIS OF MONOCYCLOPENTADIENYL COMPLEXES OF HAFNIUM AND ZIRCONIUM
LUND, EC
LIVINGHOUSE, T
[J]. ORGANOMETALLICS, 1990, 9 (09) : 2426 - 2427
[8] SYNTHETIC APPLICATIONS OF GROUP-IV METAL IMIDO COMPLEX-ALKYNE [2+2] CYCLOADDITIONS - A CONCISE TOTAL SYNTHESIS OF (+/-)-MONOMORINE
MCGRANE, PL
LIVINGHOUSE, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) : 1323 - 1324
[9] INTRAMOLECULAR [2+2] CYCLOADDITIONS OF GROUP-IV METAL IMIDO COMPLEXES - APPLICATIONS TO THE SYNTHESIS OF DIHYDROPYRROLE AND TETRAHYDROPYRIDINE DERIVATIVES
MCGRANE, PL
JENSEN, M
LIVINGHOUSE, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) : 5459 - 5460
[10] SYNTHETIC APPLICATIONS OF IMIDOTITANIUM ALKYNE [2+2] CYCLOADDITIONS - A CONCISE, STEREOCONTROLLED TOTAL SYNTHESIS OF THE ANTIFUNGAL AGENT (+)-PREUSSIN
MCGRANE, PL
LIVINGHOUSE, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (24) : 11485 - 11489

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