Syntheses and Reactions of Optically Active α-Aminoallenylstannanes

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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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0302861