Eleonóra Kiss, I. Markó, M. Guillaume
Nov 25, 2011
Citations
0
Influential Citations
3
Citations
Journal
Tetrahedron
Abstract
A new, highly enantioselective synthesis of (2S,3S)-3-amino-N-cyclopropyl-2-hydroxyhexanamide, a synthetic fragment of the experimental hepatitis C drug Telaprevir, has been described. Conjugate addition of the enantiomerically pure Davies lithium amide followed by hydroxylation of the in situ generated b-amino enolate was employed for the formation of the required stereogenic centres. Importantly, very high diastereoselectivities can still be achieved in the key-step when the relatively expensive and enantiopure (camphorsulfonyl)oxaziridine hydroxylating agent is replaced by racemic trans-N-sulfonyloxaziridines. Among the tested N-sulfonyloxaziridines the iso-propyl substituted analogue proved to be the ideal choice from an economic viewpoint.