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
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container_end_page 3449
container_issue 19
container_start_page 3447
container_title Organic letters
container_volume 5
creator Ortiz-Marciales, Margarita
González, Eduvigis
De Jesús, Melvin
Espinosa, Sandraliz
Correa, Wildeliz
Martínez, Johanna
Figueroa, Ruth
description 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.
doi_str_mv 10.1021/ol0352153
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subjects Alkylation
Borohydrides - chemistry
Boron Compounds - chemical synthesis
Ephedrine - analogs & derivatives
Lithium Compounds - chemistry
Molecular Structure
Oxazines - chemical synthesis
Phenylpropanolamine - analogs & derivatives
Stereoisomerism
title Efficient Synthesis of B-Alkylated Oxazaborolidines Derived from Ephedrine and Norephedrine
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