Synfacts 2007(12): 1291-1291  
DOI: 10.1055/s-2007-991376
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Quaternary Allylic Amines by Asymmetric Aza-Claisen Rearrangements

Contributor(s): Mark Lautens, Michael Langer
D. F. Fischer, Z.-Q. Xin, R. Peters*
ETH Zürich, Switzerland
Further Information

Publication History

Publication Date:
22 November 2007 (online)

Significance

Allylic amines are key intermediates in the synthesis of quaternary amino acids. The authors recently reported a highly active catalyst for the Overman rearrangement of E-configured allylic PMP-trifluoroacetimidates (Angew. Chem. Int. Ed. 2006, 45, 5694). They now extend this methodology to the synthesis of highly enantioenriched quaternary allylic amines. The products can be further derivatized to unsymmetrically α,α-di­substituted or β,β-disubstituted amino acids.