jo5b00529_si_002.cif (18.08 kB)

2‑Vinyl Threoninol Derivatives via Acid-Catalyzed Allylic Substitution of Bisimidates

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posted on 05.06.2015, 00:00 by Varun Kumar, Kristine Klimovica, Dace Rasina, Aigars Jirgensons
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.