Abstract
A diastereoselective synthesis of 4-vinyl oxazolines syn-2 was developed based on an acid-catalyzed cyclization of bistrichloroacetimidates (E)-1. The reaction likely involves an allyl carbenium ion intermediate in which the adjacent stereocenter directs the stereoselectivity for C-N bond formation. Oxazolines syn-2 were transformed to C-quaternary threoninol, threoninal, and threonine derivatives which can be further incorporated into complex natural compounds.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Allyl Compounds / chemistry*
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Amino Alcohols / chemistry*
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Butylene Glycols / chemistry*
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Cyclization
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Imidoesters / chemical synthesis*
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Imidoesters / chemistry
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Molecular Structure
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Oxazoles / chemical synthesis*
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Oxazoles / chemistry
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Stereoisomerism
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Vinyl Compounds / chemistry*
Substances
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2-vinyl threoninol
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Allyl Compounds
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Amino Alcohols
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Butylene Glycols
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Imidoesters
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Oxazoles
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Vinyl Compounds
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threoninol