100992-81-2Relevant academic research and scientific papers
A convenient synthesis of aziridine-2-carboxylic esters
Legters, Johan,Thijs, Lambertus,Zwanenburg, Binne
, p. 1 - 15 (2007/10/02)
Optically active oxirane-2-carboxylic esters, prepared from allylic alcohols employing the Sharpless epoxidation, were treated with sodium azide.The azido alcohols obtained were subsequently converted into aziridine-2-carboxylic esters by reaction with triphenylphosphine, in good yields and with high optical purity.Various racemic oxirane-2-carboxylic esters were subjected to the same sequence of reactions.
Selective C-2 opening of 2,3-epoxyesters with HN3-amine system: A viable route to β-hdyroxy-α-amino acids
Saito,Takahashi,Ishikawa,Moriwake
, p. 667 - 670 (2007/10/02)
The combination of hydrogen azide with amines has proven to effect the C-2 opening of 2,3-epoxyester with high regioselectivity uniformly for trans-epoxyesters and depending on their structures for cis-2,3-epoxyesters.
A CONVENIENT SYNTHESIS OF OPTICALLY ACTIVE 1H-AZIRIDINE-2-CARBOXYLIC ACIDS (ESTERS).
Legters, J.,Thijs, L.,Zwanenburg, B.
, p. 4881 - 4884 (2007/10/02)
Optically active glycidic esters, prepared from allylic alcohols employing the Sharpless epoxidation, were treated with sodium azide.In a subsequent reaction with PPh3 the azido alcohols thus obtained were converted into aziridine-2-carboxylic esters of high optical purity in good yields.
Synthesis of the optical antipodes of 4-alkyl-γ-lactones
Thijs, Lambertus,Waanders, Peter P.,Stokkingreef, Edwin H. M.,Zwanenburg, Binne
, p. 332 - 337 (2007/10/02)
Optical antipodes of 4-alkyl-γ-lactones 3 have been prepared by photochemical rearrangement of optically active α,β-epoxy diazomethyl ketones 1 in ethanol to give 4-hydroxy-alkenoates 2, followed by reduction of the alkene bond and subsequent lactonization.The required epoxy diazomethyl ketones 1 were obtained via the following sequence of reactions: alkylation of 2-propyn-1-ol, subsequent reduction to the alkenols 6, Sharpless epoxidation to 2,3-epoxy alcohols 7, oxidation to glycidic esters 8 and finally conversion to diazo ketones 1.The enantiomeric purities range from 84 to 100percent.
Enantioselective Diastereospecific Synthesis of anti-α-Alkyl-β-hydroxy Esters through Cuprate Opening of Glycidic Esters
Mulzer, Johann,Lammer, Ortrud
, p. 2178 - 2190 (2007/10/02)
A diastereospecific chain elongation of the aldehydes 1 to anti-αalkyl-β-hydroxy esters 2 via the intermediates 4 - 7 is described.By means of the Sharpless epoxidation, 2 may be obtained with >90percent ee in either enantiomer.
