Abstract
A new synthetic method for the preparation of allyl amines has been developed. The key steps of this method are enantioselective addition of diethylzinc and [1,3]-chirality transfer through the [3.3] sigmatropic rearrangement of allyl cyanates. Stereocontrolled syntheses of lentiginosine (1) and polyoxamic acid derivative 2 from a common intermediate 7 derived from D-tartaric acid (8), have been accomplished.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkaloids / chemical synthesis*
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Alkaloids / chemistry
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Allyl Compounds / chemical synthesis*
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Allyl Compounds / chemistry
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Amines / chemical synthesis*
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Amines / chemistry
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Azetidinecarboxylic Acid / analogs & derivatives*
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Azetidinecarboxylic Acid / chemical synthesis
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Azetidinecarboxylic Acid / chemistry
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Molecular Structure
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Organometallic Compounds / chemistry*
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Oxamic Acid / analogs & derivatives
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Oxamic Acid / chemical synthesis*
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Oxamic Acid / chemistry
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Stereoisomerism
Substances
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Alkaloids
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Allyl Compounds
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Amines
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Organometallic Compounds
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lentiginosine
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polyoximic acid
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Azetidinecarboxylic Acid
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Oxamic Acid
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diethylzinc