Syntheses and Reactions of Optically Active α-Aminoallenylstannanes

Lithiation/stannylation of optically active N-propargyloxazolidinones produced optically active α-oxazolidinonylallenylstannanes. Reaction of these with aldehydes in the presence of BF3·OEt2 produced β-hydroxypropargylamines with high syn diastereoselectivity and ee. These were converted to γ-hydrox...

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Veröffentlicht in:	Journal of organic chemistry 2004-01, Vol.69 (1), p.105-111
Hauptverfasser:	Ranslow, Peter B. D, Hegedus, Louis S, de los Rios, Cristobal
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Magnetic Resonance Spectroscopy Organic chemistry Oxidation-Reduction Preparations and properties Spectrophotometry, Ultraviolet Stereoisomerism Tin Compounds - chemical synthesis Tin Compounds - chemistry
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container_title	Journal of organic chemistry
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creator	Ranslow, Peter B. D Hegedus, Louis S de los Rios, Cristobal
description	Lithiation/stannylation of optically active N-propargyloxazolidinones produced optically active α-oxazolidinonylallenylstannanes. Reaction of these with aldehydes in the presence of BF3·OEt2 produced β-hydroxypropargylamines with high syn diastereoselectivity and ee. These were converted to γ-hydroxy-β-amino acids by oxidative cleavage of the alkyne.
doi_str_mv	10.1021/jo0302861
format	Article
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subjects	Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Magnetic Resonance Spectroscopy Organic chemistry Oxidation-Reduction Preparations and properties Spectrophotometry, Ultraviolet Stereoisomerism Tin Compounds - chemical synthesis Tin Compounds - chemistry
title	Syntheses and Reactions of Optically Active α-Aminoallenylstannanes
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