Highly Regio- and Stereoselective 1,1-Cycloaddition of Carbon Monoxide with 1,4-Dilithio-1,3-dienes. Novel Synthetic Methods for 3-Cyclopenten-1-one Derivatives

Song, Qiuling; Chen, Jinglong; Jin, Xianglin; Xi, Zhenfeng

doi:10.1021/ja0165638

Cited by 66 publications

(35 citation statements)

References 29 publications

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“…Since we initially noticed the novel reaction patterns of 1,4-dilithio-1,3-diene derivatives 5 in 2000, 6 we have been investigating the reactions of 5 with various organic substrates. [6][7][8][9][10][11] In order to study on the reaction of the addition intermediates 1 or 2 with nucleophiles, we used 5 as model compounds, expecting that selectivity can be improved and new types of reaction patterns can be discovered. 5 As demonstrated in Scheme 3, both carbophilic addition intermediates 6 (Scheme 3, type a) and thiophilic addition intermediates 7 (Scheme 3, type b) can be expected as the first intermediate compounds.…”

Section: Introductionmentioning

confidence: 99%

Preparation of S-containing heterocycles via novel reaction patterns of carbon disulfide with 1-lithiobutadienes and 1,4-dilithiobutadienes

Wang¹,

Chen²,

Song³

et al. 2003

Arkivoc

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Dedicated to Professor Zhitang AbstractBoth carbophilic addition and thiophilic addition were involved in the first step intermolecular reaction of 1,4-dilithio-1,3-diene derivatives with carbon disulfide. Thus in situ generated carbophilic addition intermediates and thiophilic addition intermediates underwent a second step intramolecular carbophilic and thiophilic additions. Multiply substituted thiophenes were isolated as the results of cleavage of the C=S double bonds, while thiopyran-2-thiones were produced via cycloaddition reactions. In addition to 1,4-dilithio-1,3-dienes, monolithio reagents also showed interesting reactions with carbon disulfide. Thiophenes were also generated in the reaction of 1-lithio-1,3-dienes with carbon disulfide.

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Section: Introductionmentioning

confidence: 99%

Preparation of S-containing heterocycles via novel reaction patterns of carbon disulfide with 1-lithiobutadienes and 1,4-dilithiobutadienes

Wang¹,

Chen²,

Song³

et al. 2003

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“…The corresponding derivatives were obtained in excellent yield after treating the reaction mixture with various electrophiles such as MeI and Me 2 SO 4 [47]. Recently, the key intermediate of that reaction, an oxycyclopentadienyl lithium compound, was successfully isolated as a single crystal and its structure was fully characterized [48].…”

Section: 4 14-bimetallic Compoundsmentioning

confidence: 99%

Recent developments in homobimetallic reagents and catalysts for organic synthesis

Shimeng

et al. 2011

Chin. Sci. Bull.

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Organometallics are a family of useful organic chemicals because they play important roles in organic synthesis as reagents and as catalysts. They can be classified according to the number of metals they contain. Bimetallic compounds are important organometallics and they are either homobimetallic or heterobimetallic depending on whether the two metals are the same or different. In this paper, we focus on homobimetallic compounds. Homobimetallic compounds are generally used as dianions to react with electrophiles in organic synthesis. Recently, homobimetallics have also been used as catalysts in organic reactions such as in asymmetric reactions. homobimetallics, reagent, catalyst, synthesis, application Citation:Wu W, Gu D L, Wang S M, et al. Recent developments in homobimetallic reagents and catalysts for organic synthesis.

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“…Our group has been interested in the reactivity of butadienyl lithium reagents, [46][47][48][49][50] and found that the reaction of 1-lithio-4-halo-1,3-diene [51] with group 6 metal carbonyl compounds could afford full alkyl substituted pyranylidene complexes in high yields by intramolecularly trapping the metallacyclic intermediates (Scheme 8) [52,53]. It is for the first time to prepare tetrasubstituted full alkyl substituted pyranylidene complexes.…”

Section: [4+2] Cyclizationmentioning

confidence: 99%

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

et al. 2010

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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.

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Highly Regio- and Stereoselective 1,1-Cycloaddition of Carbon Monoxide with 1,4-Dilithio-1,3-dienes. Novel Synthetic Methods for 3-Cyclopenten-1-one Derivatives

Cited by 66 publications

References 29 publications

Preparation of S-containing heterocycles via novel reaction patterns of carbon disulfide with 1-lithiobutadienes and 1,4-dilithiobutadienes

Preparation of S-containing heterocycles via novel reaction patterns of carbon disulfide with 1-lithiobutadienes and 1,4-dilithiobutadienes

Recent developments in homobimetallic reagents and catalysts for organic synthesis

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

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