C-Quaternary Vinylglycinols by Metal-Catalyzed Cyclization of Allylic

Synlett 2011
Kristīne Kļimoviča, Liene Grigorjeva, Ansis Maļeckis, Juris Popelis, Aigars Jirgensons

Bistrichloroacetimidates derived from 2-substituted but- 2-ene-1,4-diols are transformed into 4-substituted 4-vinyloxazolines in high yields and excellent regioselectivities when Lewis acids AlCl3, FeCl3, TMSOTf, BF3·OEt2, and AgBF4 are used as catalysts as well as with the Pd(PPh3)2Cl2/AgBF4 catalytic system. Lower regioselectivity is achieved with a neutral PdCl2(MeCN)2 catalyst and this could be a consequence of a switch to a competitive but less selective reaction mechanism. It is demonstrated that 4-substituted 4-vinyloxazolines can be efficiently transformed to N-Bocprotected C-quaternary vinylglycinols in a one-pot procedure.

Keywords
amino alcohols, Lewis acids, palladium, cyclization regioselectivity
DOI
10.1055/s-0031-1289537
Hyperlink
https://www.thieme-connect.com/ejournals/abstract/synlett/doi/10.1055/s-0031-1289537

Kļimoviča, K., Grigorjeva, L., Maļeckis, A., Popelis, J., Jirgensons, A. C-Quaternary Vinylglycinols by Metal-Catalyzed Cyclization of Allylic. Synlett, 2011, No. 19, pp.2849-2851. ISSN 0936-5214. e-ISSN 1437-2096. Available from: doi:10.1055/s-0031-1289537

Publication language
English (en)