Stereocontrolled formation of amino acids and N-heterocycles bearing a quaternary chiral carbon
Roy, S.ép.; Spino, C.
Organic Letters 8(5): 939-942
2006
ISSN/ISBN: 1523-7060 PMID: 16494479 DOI: 10.1021/ol053061g
Accession: 050384362
Stereocontrolled formation of tertiary or quaternary chiral carbons bearing nitrogen was achieved using the [3,3]-sigmatropic rearrangement of cyanate to isocyanate as a key element. A short and highly selective sequence of reactions, starting from p-menthane-3-carboxaldehyde, was developed leading to alpha,alpha-dialkylated alpha-amino acids or N-heterocycles, depending on the method of cleavage of the auxiliary.
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