Unsaturated Syn - and Anti -1,2-Amino Alcohols by Cyclization of Allylic Bis-Trichloroacetimidates. Stereoselectivity Dependence on Substrate Configuration

Journal of Organic Chemistry 2015
Liene Grigorjeva, Artis Kinēns, Aigars Jirgensons

Disubstituted allylic bis-imidates undergo Lewis acid catalyzed or spontaneous cyclization to oxazolines, which are precursors of unsaturated amino alcohols. Stereoselectivity of the cyclization is mainly determined by the substrate configuration. Highly selective cis-oxazoline formation is achieved starting from anti-E-bis-imidates while trans-oxazoline predominantly forms from anti-Z-bis-imidates. On the basis of DFT calculations, the stereoselectivity trends can be explained by the formation of the energetically most stable carbenium ion conformation, followed by the cyclization via most favorable bond rotations.

DOI
10.1021/jo502404y
Hipersaite
http://pubs.acs.org/doi/abs/10.1021/jo502404y

Grigorjeva, L., Kinēns, A., Jirgensons, A. Unsaturated Syn - and Anti -1,2-Amino Alcohols by Cyclization of Allylic Bis-Trichloroacetimidates. Stereoselectivity Dependence on Substrate Configuration. Journal of Organic Chemistry, 2015, Vol.80, Iss.2, 920.-927.lpp. ISSN 0022-3263. Pieejams: doi:10.1021/jo502404y

Publikācijas valoda
English (en)