Stereoselective Synthesis of anti-1,3-Aminoalcohols via Reductive Opening of 4‑Amidotetrahydropyrans Derived from the Prins/Ritter Sequence

A novel method has been devised for anti-1,3-aminoalcohols through reductive elimination of iodomethyltetrahydropyrans which are in turn derived from a Prins/Ritter reaction sequence. The synthetic versatility of this method has been explored in the total synthesis of piperidine alkaloids and β-amin...

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Veröffentlicht in:	Organic letters 2013-02, Vol.15 (3), p.546-549
Hauptverfasser:	Yadav, J. S, Jayasudhan Reddy, Y, Adi Narayana Reddy, P, Subba Reddy, B. V
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkaloids - chemical synthesis Alkaloids - chemistry Amino Acids - chemical synthesis Amino Alcohols - chemical synthesis Amino Alcohols - chemistry Combinatorial Chemistry Techniques Magnetic Resonance Spectroscopy Molecular Structure Piperidines - chemical synthesis Piperidines - chemistry Stereoisomerism
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Beschreibung
Zusammenfassung:	A novel method has been devised for anti-1,3-aminoalcohols through reductive elimination of iodomethyltetrahydropyrans which are in turn derived from a Prins/Ritter reaction sequence. The synthetic versatility of this method has been explored in the total synthesis of piperidine alkaloids and β-amino acids.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol303364j