127927-41-7Relevant academic research and scientific papers
An improved preparation of epoxides from carbonyl compounds by using diiodomethane/methyllithium: Synthetic applications
Concellón, José M,Cuervo, Humildad,Fernández-Fano, Ramón
, p. 8983 - 8987 (2007/10/03)
Synthesis of epoxides starting from different carbonyl compounds is easily carried out by using a diiodomethane and methyllithium at 0°C and a short reaction time. Starting from α-aminoaldehydes the reaction affords amino epoxides, with high diastereoselectivity. The products were transformed into 1,3-diaminoalkan-2-ols by treatment with different amines.
Iodomethylation of Chiral α-Amino Aldehydes by Means of Samarium/Diiodomethane. Application to the Synthesis of Various Enantiomerically Pure Compounds
Concellon, Jose M.,Bernad, Pablo L.,Perez-Andres, Juan A.
, p. 8902 - 8906 (2007/10/03)
Chiral iodohydrins 2 have been obtained from α-amino aldehydes 1 and Sm/CH2I2. Treatment of compound 2 with acetic anhydride, NaH, or AgBF4 affords, with high diastereoselectivity, O-protected 3-(dibenzylamino)-1-iodoalkan-2-ol 3, amino epoxides 4, or azetidinium salts 5, respectively. The synthesis of enantiomerically pure allylamines 6 is also described by metallation of 3 with zinc. The reaction of α-amino aldehydes 1 with Sm/CH2I2 and further treatment with organocuprates affords chiral amino alcohols 7 in a one-pot process.
Preparation of aminoalkyl chlorohydrin hydrochlorides: Key building blocks for hydroxyethylamine-based HIV protease inhibitors
Beaulieu, Pierre L.,Wernic, Dominik
, p. 3635 - 3645 (2007/10/03)
Enantiomerically pure N,N-dibenzyl-α-amino aldehydes reacted with (chloromethyl)lithium, generated in situ from bromochloromethane and lithium metal, to give predominantly erythro aminoalkyl epoxides. Treatment of the crude epoxides with aqueous hydrochloric acid gave crystalline (2S,3S)-N,N-dibenzylamino chlorohydrin hydrochlorides in 32-56% overall yield and high isomeric purity. These compounds are versatile synthetic intermediates for the preparation of hydroxyethylamine-based HIV protease inhibitors, either directly as such, or via conversion to the corresponding N-Boc(2S,3S)-aminoalkyl epoxides. The processes described do not make use of hazardous reagents or intermediates, do not require chromatographic purifications, and are thus amenable to the preparation of large quantities of these versatile building blocks.
Highly Diastereoselective Synthesis of Threo or Erythro Aminoalkyl Epoxides from α-Amino Acids
Barluenga, Jose,Baragana, Beatriz,Concellon, Jose M.
, p. 6696 - 6699 (2007/10/03)
α-Chloro-α'-(dibenzylamino)methylketones 3 are synthesized in enantiomerically pure form starting from α-amino acids.Reduction of amino ketones 3 and further epoxidation affords threo aminoalkyl epoxides 6 with diastereoisomeric excess ranging between 94percent and 98percent.The synthesis of erythro amino epoxides 9 is also described by reaction of α-amino aldehydes 7 with in situ generated (halomethyl)lithium.Amino epoxides 9 were obtained with a diastereoisomeric excess ranging between 91percent and 98percent.
The First Direct Preparation of Chiral Functionalised Ketones and their Synthetic Uses
Barluenga, Jose,Baragana, Beatriz,Alonso, Alejandro,Concellon, Jose M.
, p. 969 - 970 (2007/10/02)
Almost enantiomerically pure halogenated α-hydroxy and α-amino ketones can be prepared from O-protected lactates and tribenzylated alanine, respectively; whilst amino ketones 3g have also been transformed into the amine epoxide 7 with high diastereoselect
PROTECTIVE GROUP TUNING IN THE STEREOSELECTIVE CONVERSION OF α-AMINO ALDEHYDES INTO AMINOALKYL EPOXIDES
Reetz, M.T.,Binder, J.
, p. 5425 - 5428 (2007/10/02)
Sulfonium and arsonium ylides of the type CH2=S(CH3)2 and CH2=As(Ph)3 react with doubly protected α-amino aldehydes 1 derived from amino acids to form aminoalkyl epoxides 3/4, diastereofacial selectivity ranging between 86:14 and >95:5.
