Lithium‐diazoessigsäure‐äthylester

Schöllkopf, Ulrich; Frasnelli, Hubert

doi:10.1002/ange.19700820705

Cited by 27 publications

(2 citation statements)

References 6 publications

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“…Metalation of diazo compounds by metal amides, [21] by nBuLi, [22] by silver(I) oxide, [23] and by mercuric oxide [24] are well known. Although there have been no examples of related gold diazo compounds, to our knowledge, gold alkoxides have been shown to deprotonate carbonyl compounds such as methyl cyanoacetate to form the resulting C-bound gold(I) enolates.…”

mentioning

confidence: 99%

Reactions of a Stable Monomeric Gold(I) Hydride Complex

2008

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mentioning

confidence: 99%

Reactions of a Stable Monomeric Gold(I) Hydride Complex

2008

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“…0 -C(N,) vector, corresponding to its formation, and no net reaction occurs. The only possible reaction, exothermic with respect to the reactants, is formation of the Ge=N species (24). Since this is of higher energy than (25), it is conceivable that N, could under experimental conditions be extruded from preformed…”

Section: And>2n and Is A Direct Acyclic Analogue Of Compounds (5)-(8)mentioning

confidence: 99%

Formation of germanium–nitrogen double bonds in reactions of the electron-rich germylene bis[bis(trimethylsilyl)amido]germanium(II) with a range of diazo-compounds

Glidewell¹,

Lloyd²,

Lumbard³

1987

J. Chem. Soc., Dalton Trans.

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The electron-rich germylene Ge[N (SiMe,),], reacts w i t h the diazo-compounds R'CH,COC(N,) R2 [R1 = H, R2 = CO(OEt), SO,C,H,Me-p, or COPh; R1, R2 = -CMe,CH,C(O)-1, which contain an enolisable function, t o yield the heterocycles de[N(SiMe,),],NHN=C( R2)C(=CH R1)b; the weakly acidic diazo-compounds ethyl diazoacetate and diazoacetophenone yield bis-adducts Ge[N(SiMe,),],[C(N,)COR][NHN=C(H)COR] (R = OEt or Ph). Diazo-compounds containing two non-enolisable substituents yield mono-adducts w i t h Ge[N (SiMe,),],which can be hydrolysed t o yield the diol Ge(OH),[N(SiMe,),], and, in one example, the corresponding hydrazone H,NN= C( COPh)CO(OEt). These adducts appear to be thermodynamically stable in an aprotic solvent, but can be trapped b y addition of ethanol, t o yield Ge[N(SiMe,),],(OEt){NHN=C[CCO(OMe)]2}, or of diazoacetophenone to yield Ge[ (SiMe,),],[ C( N, ) COPhj{ N H N=C [CO( OMe)],}. All the reactions of the germylene with diazo-compounds can be rationalised in terms of the initial formation of a germyleneazine [ (Me,Si),N],Ge=N-N=C(X)Y, which readily adds any available protic species t o give a germane derivative. M N D O calculations o n model systems are in accord with the experimental findings and also explain their differences from results previously obtained using the simpler germylene GePh,.

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The First Catalytic Enantioselective Aldol‐Type Reaction of Ethyl Diazoacetate to Ketones

2009

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Abstract:The aldol-type addition to ketones still represents a great challenge in asymmetric catalysis. Recently, the direct aldol reaction between the commercially available ethyl diazoacetate and aldehydes has attracted increasing attention. Ethyl diazoA C H T U N G T R E N N U N G acetate is economical and allows further transformation of the aldol adduct obtained. We present a solution for the arduous, and not previously described, addition of diazoacetate to ketones. Our procedure employs commercially available nor-A C H T U N G T R E N N U N G ephedrine-derived ligands and dialkylzinc reagents [R 2 Zn: (diethylzinc, Et 2 Zn; dimethylzinc, Me 2 Zn)] as starting materials, therefore the active catalyst is prepared with a very straightforward methodology. Remarkably, the reaction gives good enantiomeric excesses with a-halo ketones, a class of compounds that has not been commonly used in enolate addition.

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Lithium‐diazoessigsäure‐äthylester

Cited by 27 publications

References 6 publications

Reactions of a Stable Monomeric Gold(I) Hydride Complex

Reactions of a Stable Monomeric Gold(I) Hydride Complex

Formation of germanium–nitrogen double bonds in reactions of the electron-rich germylene bis[bis(trimethylsilyl)amido]germanium(II) with a range of diazo-compounds

The First Catalytic Enantioselective Aldol‐Type Reaction of Ethyl Diazoacetate to Ketones

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