Stereoselective construction of 3a-methylhydrindanes starting from 2,7-enynol derivatives based on Ti(II)-mediated cyclization and Ru-catalyzed ring-closing metathesis

Ohkubo, Mutsumi; Uchikawa, Wataru; Matsushita, Hitomi; Nakano, Aiko; Shirato, Takayuki; Okamoto, Sentaro

doi:10.1016/j.tetlet.2006.05.030

Cited by 9 publications

(1 citation statement)

References 36 publications

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“…The substrates meta -methyl benzyl chloride ( 1k ), meta -phenyl benzyl chloride ( 1l ), and meta -allyl benzyl chloride ( 1m ) also underwent the expected allylation reaction smoothly to produce the para -allylated benzene derivatives 3k – 3m in satisfactory to good yields (entries 11–13, 72–88%). The product 3m having two adjacent allyl groups could be converted to 6-methyl-1,4-dihydronaphthalene via a ruthenium-catalyzed metathesis reaction . The reactivities of benzyl chloride substrates 1n – 1p having two methyl groups linked on benzene rings were subsequently investigated.…”

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confidence: 99%

Palladium-Catalyzed sp²–sp³ Coupling of Chloromethylarenes with Allyltrimethoxysilane: Synthesis of Allyl Arenes

et al. 2017

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confidence: 99%

Palladium-Catalyzed sp²–sp³ Coupling of Chloromethylarenes with Allyltrimethoxysilane: Synthesis of Allyl Arenes

et al. 2017

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The Krapcho Dealkoxycarbonylation Reaction of Esters with α‐Electron‐Withdrawing Substituents

Krapcho

Ciganek

2013

Organic Reactions

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The Krapcho reaction involves esters with α‐electron‐withdrawing substituents such as malonates, β‐keto esters, and α‐cyano esters, which undergo dealkoxycarbonylation on being heated in polar aprotic solvents (such as DMSO, DMF, or HMPT) in the presence of water, or in polar aprotic solvents with water in the presence of added salts (such as NaCN, NaCl, LiCl, LiI, or MgCl 2 ). This procedure avoids the use of strongly aqueous acidic and alkaline conditions and tolerates many functional and protecting groups. The chapter presents the mechanistic aspects of this procedure, which include reaction parameters such as solvents, salts, other additives, and the use of microwave irradiation. The diastereoselectivity of protonation of the enolate intermediate leading to the dealkoxycarbonylated products is discussed. Trapping of the intermediate enolate by electrophiles other than a proton is illustrated. Potential side reactions and same‐pot subsequent reactions of substrates are discussed along with functional‐group compatibility for halogens and nitrogen, oxygen, sulfur, selenium, and carbon functional groups. Several examples of applications of this methodology for the synthesis of natural products along with experimental conditions and procedures are presented. Closely related methods are discussed in the Comparison with Other Methods section. The tables, which consist of 371 pages, are grouped according to substrate structure. Selective entries for other methods (excluding classical aqueous acidic or basic methods) are included in the tabular survey for comparative purposes.

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Olefin Ring‐Closing Metathesis

Yet

2016

Organic Reactions

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The olefin ring‐closing metathesis reaction catalyzed by ruthenium and molybdenum complexes has been employed in the syntheses of carbocycles, heterocycles, supramolecular compounds, and in tandem metathesis reactions. Chiral ruthenium and molybdenum catalysts have provided high enantiomeric and diastereomeric excesses in ring‐closing metathesis reactions. Many of the unsuccessful medium‐ and large‐sized ring formations which were unsuccessful by traditional methods, such as the intramolecular Wittig, Horner–Wadsworth–Emmons, and Julia–Kocienski reactions, can now be formed by olefin ring‐closing metathesis reactions. Ring‐closing metathesis has been a key step and sometimes the only successful method for the synthesis of numerous natural products and drug discovery targets. The objective of this chapter is to provide an updated, comprehensive coverage of the literature of the olefin ring‐closing metathesis reaction and related processes. Key mechanistic points are summarized.

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Stereoselective construction of 3a-methylhydrindanes starting from 2,7-enynol derivatives based on Ti(II)-mediated cyclization and Ru-catalyzed ring-closing metathesis

Abstract: 2 /ZnX 2 effectively reduced ketones and imines in the presence of a Lewis Acid.Leave this area blank for abstract info.

Cited by 9 publications

References 36 publications

Palladium-Catalyzed sp²–sp³ Coupling of Chloromethylarenes with Allyltrimethoxysilane: Synthesis of Allyl Arenes

Palladium-Catalyzed sp²–sp³ Coupling of Chloromethylarenes with Allyltrimethoxysilane: Synthesis of Allyl Arenes

The Krapcho Dealkoxycarbonylation Reaction of Esters with α‐Electron‐Withdrawing Substituents

Olefin Ring‐Closing Metathesis

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Stereoselective construction of 3a-methylhydrindanes starting from 2,7-enynol derivatives based on Ti(II)-mediated cyclization and Ru-catalyzed ring-closing metathesis

Abstract: 2 /ZnX 2 effectively reduced ketones and imines in the presence of a Lewis Acid.Leave this area blank for abstract info.

Cited by 9 publications

References 36 publications

Palladium-Catalyzed sp2–sp3 Coupling of Chloromethylarenes with Allyltrimethoxysilane: Synthesis of Allyl Arenes

Palladium-Catalyzed sp2–sp3 Coupling of Chloromethylarenes with Allyltrimethoxysilane: Synthesis of Allyl Arenes

The Krapcho Dealkoxycarbonylation Reaction of Esters with α‐Electron‐Withdrawing Substituents

Olefin Ring‐Closing Metathesis

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Product

Resources

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Palladium-Catalyzed sp²–sp³ Coupling of Chloromethylarenes with Allyltrimethoxysilane: Synthesis of Allyl Arenes

Palladium-Catalyzed sp²–sp³ Coupling of Chloromethylarenes with Allyltrimethoxysilane: Synthesis of Allyl Arenes