Homopyrroles by Metal-Mediated Cycloadditions of (<i>NH</i>)-Enamines to Alkynylcarbene Tungsten Complexes<i>via</i>1-Metalla-1,3,5-Trienes

Aumann, Rudolf; Kößmeier, Michael; Roths, Klaus; Fröhlich, Roland

doi:10.1055/s-1994-23079

Cited by 39 publications

(20 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1). 17 It was envisioned that the preparation of the 1,2,3,5-tetrasubstituted pyrrole 6c could be achieved via a three-component reaction. Preliminary assays employed complex 1a, 4-fluoro benzaldehyde (8) and glycine methyl ester hydrochloride (7) as substrates (Scheme 3).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of novel polysubstituted N-benzyl-1H-pyrroles via a cascade reaction of alkynyl Fischer carbenes with α-imino glycine methyl esters

et al. 2015

View full text Add to dashboard Cite

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis of novel polysubstituted N-benzyl-1H-pyrroles via a cascade reaction of alkynyl Fischer carbenes with α-imino glycine methyl esters

et al. 2015

View full text Add to dashboard Cite

show abstract

“…These facts inspired us to develop a complementary Pauson–Khand cyclopentenone approach (Scheme ) that is based on 1) simplicity (short experimental protocol and readily available substrates and reagents), and 2) the use of recyclable [M(CO) 6 ]12 as the source of CO. Overall, the strategy requires a bromoalkene, [M(CO) 6 ], and an alkyne to generate the cyclopentene ring 3 by cyclization of the corresponding alkenyl lithium 2 and alkynylcarbene complex 1 derivatives 13…”

Section: Methodsmentioning

confidence: 99%

Regio‐ and Stereoselective Synthesis of Cyclopentenones: Intermolecular Pseudo‐Pauson–Khand Cyclization

et al. 2011

View full text Add to dashboard Cite

Zwei Schritte genügen: Ein sehr einfacher zweistufiger Zugang zu polysubstituierten Cyclopentenonen aus endständigen Alkinen, [M(CO)6] und Bromalkenen wird beschrieben. Das Protokoll ist eine Alternative zur Pauson‐Khand‐Reaktion und lässt sich auf verschiedenste Bromalkene anwenden. Die enantiomerenreinen Cyclopentenon‐Produkte können mit einem vollständig C‐substituierten quartären Stereozentrum erhalten werden.

show abstract

“…Initially, when they attempted to prepare different kinds of α,β-unsaturated Fischer carbene complexes, the reaction of hydroxybenzaldehyde 12 with methyl ethoxycarbene complex 11 was found to accidentally yield the benzopyranylidene complex 13 in 82% yield in the presence of Et 3 N (eq. (3)) [27][28][29][30][31][32][33][34][35][36][37][38][39].…”

Section: [3+3] Cyclizationmentioning

confidence: 99%

“…To obtain butadienyl carbene complexes, a Michael-type addition of 4-amino-pent-3-en-ones to alkynylcarbene complex was investigated and found to give rise to a mixture of 1,2-dihydropyridin-2-ylidene complex 16 and pyranylidene complex 17 in dichloromethane in the presence of Et 3 N [28,29], owing to the competing attack of the nitrogen and the oxygen atom on the carbene carbon before a ring closure process (eq. (4)).…”

Section: [3+3] Cyclizationmentioning

confidence: 99%

Advances in the synthesis and reactivity of 2-pyranylidene carbene complexes

et al. 2010

View full text Add to dashboard Cite

Pyranylidene carbene complexes bearing a pyran ring carbene ligand represent a unique kind of organometallic species due to their special structures and reactivity. In this review, we present a comprehensive summary on the synthesis and reactivity of pyranylidene carbene complexes during the past four decades. 2-pyranylidene carbene complexes, synthesis, reactivity Citation:Wang Q F, Zhang W X, Lin C, et al. Advances in the synthesis and reactivity of 2-pyranylidene carbene complexes.Fischer-type carbene complexes are among the most important organometallic compounds, and these have experienced a considerable surge in recent times because of their widespread application in synthetic organic chemistry since the first carbene complex was reported by Fischer and coworkers in 1964 [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18]. During the course of the development of Fischer-type carbene complexes, unsaturated Fischer carbene complexes, in which unsaturated substituents are attached to the carbene carbon center, occupy an important status owing to their good reactivity in Michael-type reactions, cycloaddition reactions, transmetalation reactions. The strong electron-withdrawing property of the pentacarbonyl metal moiety and the electron-deficient property of the β-position carbon resulting from electron-transfer from the carbene center play a cooperative effect on the versatile reactivity of unsaturated Fischer carbene complexes [2-18]. 2-Pyranylidene metal carbene complexes bearing a pyran ring carbene ligand are a special kind of unsaturated Fischer carbene complex, that has received much less attention probably because of their limitation of the synthetic methodology. Recently, some important progress has been made *Corresponding author (email: zfxi@pku.edu.cn) by the chemical community. Here we give a comprehensive review of the synthesis and reactivity of the 2-pyranylidene metal carbene complex during the past four decades.

show abstract

Homopyrroles by Metal-Mediated Cycloadditions of (NH)-Enamines to Alkynylcarbene Tungsten Complexesvia1-Metalla-1,3,5-Trienes

Cited by 39 publications

References 0 publications

Synthesis of novel polysubstituted N-benzyl-1H-pyrroles via a cascade reaction of alkynyl Fischer carbenes with α-imino glycine methyl esters

Synthesis of novel polysubstituted N-benzyl-1H-pyrroles via a cascade reaction of alkynyl Fischer carbenes with α-imino glycine methyl esters

Regio‐ and Stereoselective Synthesis of Cyclopentenones: Intermolecular Pseudo‐Pauson–Khand Cyclization

Advances in the synthesis and reactivity of 2-pyranylidene carbene complexes

Contact Info

Product

Resources

About