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Synfacts 2006(4): 0367-0367
DOI: 10.1055/s-2006-932047
DOI: 10.1055/s-2006-932047
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Enantiopure Allyl Amines Using Reductive Alkylation
J. M. Concellon*, J. R. Suarez, V. del Solar
Facultad de Quimica Universidad de Oviedo, Spain
Further Information
Publication History
Publication Date:
24 March 2006 (online)
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.