Analogues of key precursors of aspartyl protease inhibitors: Synthesis of trifluoromethyl amino epoxides

…, B Crousse, JP Bégué, D Bonnet-Delpon

Index: Nguyen, Thi Ngoc Tam; Magueur, Guillaume; Ourevitch, Michele; Crousse, Benoit; Begue, Jean-Pierre; Bonnet-Delpon, Daniele Journal of Organic Chemistry, 2005 , vol. 70, # 2 p. 699 - 702

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Citation Number: 48

Abstract

The synthesis of the title compound is described through original and tailored synthetic protocols. The addition of vinylmagnesium bromide to CF3-N-aryl and N-alkyl aldimines was efficient and did not require an activating N-substituent. The resultant CF3-allylamines were converted in an efficient and completely stereoselective route to syn CF3-epoxides 3 via formation of bromhydrins 8. The same sequence performed from the aldimine substituted ...