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

Journal of Organic Chemistry 2015
Varun Kumar, Kristīne Kļimoviča, Dace Rasiņa, 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.

DOI
10.1021/acs.joc.5b00529
Hyperlink
http://pubs.acs.org/doi/abs/10.1021/acs.joc.5b00529

Kumar, V., Kļimoviča, K., Rasiņa, D., Jirgensons, A. 2-Vinyl Threoninol Derivatives via Acid-Catalyzed Allylic Substitution of Bisimidates. Journal of Organic Chemistry, 2015, Vol.80, Iss.11, pp.5934-5943. ISSN 0022-3263. e-ISSN 1520-6904. Available from: doi:10.1021/acs.joc.5b00529

Publication language
English (en)