Convenient Preparation of Ferrocenyl Esters and Ethers

Akabori, Sadatoshi; Satô, Masaru; Ebine, Seiji

doi:10.1055/s-1981-29413

Cited by 12 publications

(10 citation statements)

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“…However, in no case did we isolate a biferrocene as a byproduct. The stable chiral acyloxyferrocene complexes 29 and 30 might be interesting precursors of various chiral alkoxyferrocenes by applying reactions already reported for acetoxy ferrocene 35 and 1,1′-diacetoxyferrocene. 36 Inspired by the very rich chemistry of o-aminobenzaldehyde and o-aminophenyl ketones for the preparation of various heterocyclic compounds, 37 we decided to synthesize the unknown chiral 2-amino-1-formyl ferrocene 33a starting from acetal 15.…”

Section: Resultsmentioning

confidence: 97%

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An Efficient Asymmetric Synthesis of 2-Substituted Ferrocenecarboxaldehydes

et al. 1997

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Ferrocenecarboxaldehyde is readily transformed into the acetal of (S)-1,2,4-butanetriol (1,3-dioxane structure) and further methylated to give acetal 15. This can then be ortho-lithiated using t-BuLi with very high diastereoselectivity (98% de). Electrophilic quenching provided a large array of compounds of established stereochemistry. Controlled hydrolysis leads to many ortho-substituted ferrocenecarboxaldehydes (98% ee) which themselves are starting materials in the synthesis of various classes of enantiopure ferrocene derivatives with planar chirality of predictable absolute configuration.

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Section: Resultsmentioning

confidence: 97%

Section: Resultsmentioning

confidence: 99%

An Efficient Asymmetric Synthesis of 2-Substituted Ferrocenecarboxaldehydes

et al. 1997

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“…3 Iodoferrocene (1) is one of the very useful building blocks for ferrocene chemistry. [4][5][6][7][8][9][10] Recently two new methods for the synthesis of 1 were reported, 11,12 both involving lithiation of ferrocene followed by reaction with tributyltin chloride to give a mixture of mono-and bis-tributylstanylferrocene, which had to be separated prior to reaction with iodine or iodine chloride to give 1. However, these procedures constituted a considerable improvement over the previously reported methods, 13 which include the reaction of ferrocenemercurio compounds with N-iodosuccinimide.…”

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confidence: 99%

A New Preparation of Iodoferrocene†

Kamounah¹,

Christensen²

1997

J. Chem. Res.

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“…Due to relative instability its chemistry is not fully developed yet. Ferrocenol esters were synthesized by acylation of ferrocenol with carboxylic acid chlorides [41], but the more convenient method for their preparation is Cu-assisted reaction of haloferrocenes with carboxylic acids [39] [42]- [44]. Here we present a preparative route to ferrocenol esters from easily available ferroceneboronic acid [45]- [47], avoiding isolation of hydroxyferrocene.…”

Section: Introductionmentioning

confidence: 99%