op6b00058_si_001.pdf (4.06 MB)

Proposed Mechanism for the Enantioselective Alkynylation of an Aryl Trifluoromethyl Ketone, the Key Step in the Synthesis of Efavirenz

Download (4.06 MB)
journal contribution
posted on 15.03.2016, 00:00 by Gareth J. Griffiths, Aleksander Warm
The rationalization of observations made during optimization of the zinc-mediated enantioselective addition of cyclopropylacetylene (2) to ketoaniline 8 in the presence of (1R,2S)-1-phenyl-2-(pyrrolidin-1-yl)­propan-1-ol (3) to afford amino alcohol 11 has enabled us to propose a mechanism for this transformation. The proposed mechanism has been used as the basis for the development of a spreadsheet-based mass-balance simulation, which has proved useful in predicting the effects of stoichiometry changes and in process troubleshooting.

History

Exports