Abstract
A stereocontrolled route via allyl 1,2-diols to vicinal diamines based on the [3.3] sigmatropic rearrangement of allyl cyanate has been developed. Our approach consists of two consecutive steps: stereoselective construction of allyl anti- and syn-1,2-diols followed by [1,3]-chirality transfer by sigmatropic rearrangement, which allow an access to anti-(2R,3R)- and syn-(2R,3S)-2,3-diaminobutanoic acids. [reaction: see text]
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Acetaldehyde / chemistry
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Allyl Compounds / chemistry*
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Aminobutyrates / chemical synthesis*
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Diamines / chemical synthesis*
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Indicators and Reagents
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Isocyanates / chemistry*
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Ketones / chemistry
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Molecular Conformation
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Organophosphonates / chemistry
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Reducing Agents
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Stereoisomerism
Substances
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Allyl Compounds
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Aminobutyrates
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Diamines
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Indicators and Reagents
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Isocyanates
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Ketones
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Organophosphonates
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Reducing Agents
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allyl isocyanate
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2,3-diaminobutanoic acid
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Acetaldehyde