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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Bibliographic Details
Published in:Organic letters 2013-02, Vol.15 (3), p.546-549
Main Authors: Yadav, J. S, Jayasudhan Reddy, Y, Adi Narayana Reddy, P, Subba Reddy, B. V
Format: Article
Language:English
Subjects:
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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Summary: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