One‐Step Homologation of Acetylenes to Allenes: 4‐Hydroxynona‐1,2‐diene

Crabbé, Pierre; Nassim, Bahman; Robert‐Lopes, Maria‐Teresa

doi:10.1002/0471264180.os063.26

Cited by 8 publications

(11 citation statements)

References 7 publications

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“…[12] Initially attempted carbocyclization of 1a with Me 3 GeSnBu 3 Scheme 1. To investigate the sequence outlined in Scheme 1, we began with 1a as a starting material; this compound was readily prepared in quantity from N,N-dipropargyl-p-toluenesulfonamide by a Crabbé reaction.…”

Section: Resultsmentioning

confidence: 99%

A Stereoselective Carbocyclization of Bis(allenes) with Germylstannane Catalyzed by Palladium Complexes

et al. 2004

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Diastereoselective germastannylation of bis(allenes) with germylstannanes, catalyzed by palladium complexes, for the construction of cis or trans five‐membered cyclic systems has been investigated. We observed that the relative stereochemical arrangements of the reaction products depends on the substituents in the reagents containing Ge−Sn σ‐bonds. When the reagent Ph3GeSnBu3 was employed in the Pd0‐catalyzed carbocyclization of bis(allenes), trans‐cyclized products and/or cis‐fused bicyclic dienes were produced. In contrast, cis cyclic compounds were obtained, again along with cis‐fused bicyclic dienes, from the reaction with Bu3GeSnBu3. NMR experiments to establish the stereochemical relationships and a mechanistic speculation for this transformation as a possible explanation for the different stereochemical outcomes are also described. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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Section: Resultsmentioning

confidence: 99%

A Stereoselective Carbocyclization of Bis(allenes) with Germylstannane Catalyzed by Palladium Complexes

et al. 2004

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“…Dioxane was dried over sodium wire with benzophenone as indicator and distilled freshly before use. n ‐Pr 2 NH, n‐ Bu 2 NH, and i‐ Bu 2 NH were dried over anhydrous barium oxide and distilled 12. All the temperatures stated refer to the oil baths used.…”

Section: Methodsmentioning

confidence: 99%

Copper (I) Iodide‐Catalyzed One‐Step Preparation of Functionalized Allenes from Terminal Alkynes: Amine Effect

Kuang

Luo

2012

Adv Synth Catal

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“…Since its development in 1979, the Crabbé reaction has proven to be a useful method for the construction of monosubstituted allenes from terminal acetylenic precursors (Scheme 53). [144][145][146][147] The reaction mechanism consists of a copper-catalyzed addition of 185 onto iminum ion 188, which is formed in situ from paraformaldehyde and diisopropylamine.…”

Section: Crabbé Homologation Reactionmentioning

confidence: 99%

Synthesizing Allenes Today (1982-2006)

Brummond¹,

DeForrest²

2007

Synthesis

343

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Allenes have allowed chemists to access a variety of structurally interesting and biologically active products. The emergence of these unique compounds in organic synthesis is a direct result of the discovery and development of efficient protocols for their preparation. Moreover, efficient syntheses of the allenyl functionality are important to the synthetic community and will be reported and discussed in this review.

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One‐Step Homologation of Acetylenes to Allenes: 4‐Hydroxynona‐1,2‐diene

Abstract: One‐Step Homologation of Acetylenes to Allenes: 4‐Hydroxynona‐1,2‐diene product: 4‐hydroxynona‐1,2‐diene

Cited by 8 publications

References 7 publications

A Stereoselective Carbocyclization of Bis(allenes) with Germylstannane Catalyzed by Palladium Complexes

A Stereoselective Carbocyclization of Bis(allenes) with Germylstannane Catalyzed by Palladium Complexes

Copper (I) Iodide‐Catalyzed One‐Step Preparation of Functionalized Allenes from Terminal Alkynes: Amine Effect

Synthesizing Allenes Today (1982-2006)

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