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Analogues of Key Precursors of AspartylProtease Inhibitors: Synthesis ofTrifluoromethyl Amino Epoxides
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The synthesis of the title compound is described throughoriginal and tailored synthetic protocols. The addition ofvinylmagnesium bromide to CF3-N-aryl and N-alkyl aldimines was efficient and did not require an activatingN-substituent. The resultant CF3-allylamines were converted in an efficient and completely stereoselective routeto syn CF3-epoxides 3 via formation of bromhydrins 8. Thesame sequence performed from the aldimine substitutedwith the methyl ether of the (R)-phenylglycinol provided thehomochiral (R,R)-amino epoxide (de >98%). This study hasallowed access to the novel racemic and homochiral trifluoromethyl β-amino epoxides, analogues of key precursors ofvarious HIV protease inhibitors.
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