Efficient Synthesis of B-Alkylated Oxazaborolidines Derived from Ephedrine and Norephedrine

Efficient Synthesis of B-Alkylated Oxazaborolidines Derived from Ephedrine and Norephedrine

Representative B-butyl- and B-methyl-1,3,2-oxazaborolidines derived from ephedrine and norephedrine were prepared in good yield and excellent purity by one-pot treatment of B-H oxazaborolidines with the corresponding organolithium reagent and subsequent hydrolysis of the cyclic borohydride intermedi...

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Veröffentlicht in:Organic letters 2003-09, Vol.5 (19), p.3447-3449
Hauptverfasser: Ortiz-Marciales, Margarita, González, Eduvigis, De Jesús, Melvin, Espinosa, Sandraliz, Correa, Wildeliz, Martínez, Johanna, Figueroa, Ruth
Format: Artikel
Sprache:eng
Schlagworte:
Alkylation
Borohydrides - chemistry
Boron Compounds - chemical synthesis
Ephedrine - analogs & derivatives
Lithium Compounds - chemistry
Molecular Structure
Oxazines - chemical synthesis
Phenylpropanolamine - analogs & derivatives
Stereoisomerism
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Beschreibung
Zusammenfassung:Representative B-butyl- and B-methyl-1,3,2-oxazaborolidines derived from ephedrine and norephedrine were prepared in good yield and excellent purity by one-pot treatment of B-H oxazaborolidines with the corresponding organolithium reagent and subsequent hydrolysis of the cyclic borohydride intermediate with anhydrous ammonium chloride.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0352153