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Synfacts 2008(12): 1311-1311
DOI: 10.1055/s-0028-1083597
DOI: 10.1055/s-0028-1083597
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New YorkCyclization of α-Amino Alkyllithium Reagents via Carbolithiation
Contributor(s):Paul Knochel, Andreas J. WagnerR. J. Bahde, S. D. Rychnovsky*
University of California, Irvine, USA
Cyclization via Carbolithiation of α-Amino Alkyllithium Reagents
Org. Lett. 2008, 10: 4017-4020
University of California, Irvine, USA
Cyclization via Carbolithiation of α-Amino Alkyllithium Reagents
Org. Lett. 2008, 10: 4017-4020
Further Information
Publication History
Publication Date:
20 November 2008 (online)
Key words
spiro compounds - annulation - alkyllithium reagents
Significance
A new route to tertiary α-amino stereocenters by carbolithiation of alkylated aminonitriles is reported. The cyclic or spirocyclic products are obtained in satisfactory yields and moderate to high diastereoselectivities.
Comment
The powerful reducing agent LiDBB allows a direct metalation of aminonitriles. This new type of annulation reaction is a promising tool in the synthesis of alkaloid structures and is applicable both to cyclic and acyclic amines.