2-Vinyl Threoninol Derivatives via Acid-Catalyzed Allylic Substitution of Bisimidates
Varun Kumar1, Kristine Klimovica1, Dace Rasina1
1Latvian Institute of Organic Synthesis, Aizkraukles 21, Riga, Latvia LV 1006.
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.
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