Synthesis of Enantiopure Allyl Amines Using Reductive Alkylation

Significance

Enantiopure allyl amines were synthesized in very high yields with complete regio- and stereocontrol using a reductive alkylation of the enantiopure aminoalkyl epoxides. A range of alkyl and aryl R¹ and R² groups were demonstrated including Me, n-alkyl, i-Pr, t-Bu and Ph. The mechanism is proposed to proceed via the anion A, which undergoes an α-elimination to generate the carbenoid B. An insertion of the carbene into the organolithium followed by elimination of lithium oxide yields the allyl amine. Both cis and trans amino epoxides gave E-selectivity.