Allyl cyanate-to-isocyanate rearrangement for the synthesis of quaternary stereocenter with nitrogen substituent

The stereochemistry and efficiency of an allyl cyan-ate-to-isocyanate rearrangement for the construction of quaternary stereocenter with nitrogen substituent was investigated by the synthesis of (R)-alpha-methylphenylala-nine. The rearrangement was found to be stereospecificity, and the chirality of...

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Bibliographic Details
Published in:Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2005-05, Vol.69 (5), p.939-943
Main Authors: Ichikawa, Y. (Kochi Univ. (Japan). Faculty of Science), Yamauchi, E, Isobe, M
Format: Article
Language:English
Subjects:
Allyl Compounds - chemistry
amino acid
AMINO COMPOUNDS
Biological and medical sciences
CARBAMATES
CHEMICAL SYNTHESIS
Cyanates - chemistry
Fundamental and applied biological sciences. Psychology
INFRARED SPECTROPHOTOMETRY
ION EXCHANGE CHROMATOGRAPHY
Isocyanates - chemistry
ISOMERIZATION
methylphenylalanine
Models, Chemical
Molecular Conformation
Molecular Structure
natural products
NITROGEN
NMR SPECTROSCOPY
Phenylalanine - analogs & derivatives
Phenylalanine - chemical synthesis
rearrangement
Stereoisomerism
THIN LAYER CHROMATOGRAPHY
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Summary:The stereochemistry and efficiency of an allyl cyan-ate-to-isocyanate rearrangement for the construction of quaternary stereocenter with nitrogen substituent was investigated by the synthesis of (R)-alpha-methylphenylala-nine. The rearrangement was found to be stereospecificity, and the chirality of allyl carbamate was transferred to that of the quaternary carbon bearing isocyanate group. These results establish that an allyl cyanate-to-isocyanate rearrangement is a useful method for the synthesis of natural products, that contain the quaternary carbon with nitrogen substituent.
ISSN:0916-8451
1347-6947
DOI:10.1271/bbb.69.939