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Synfacts 2010(12): 1392-1392  
DOI: 10.1055/s-0030-1258882
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Chiral N-Heterocycles via Asymmetric Allylic Methylation-Ring-Closing Metathesis

Contributor(s): Mark Lautens, Norman Nicolaus
J. F. Teichert, S. Zhang, A. W. van Zijl, J. W. Slaa, A. J. Minnaard, B. L. Feringa*
University of Groningen, The Netherlands
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Publication History

Publication Date:
22 November 2010 (online)

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Significance

A short and efficient sequence for the enantioselective preparation of chiral six-, ­seven-, and eight-membered N-heterocycles is described. The chirality is introduced by an asymmetric copper-catalyzed allylic methylation on readily available allylic bromides of type 1 and 2. The chiral alkylation products (3 and 4) could be transformed into the desired N-heterocycles of type 5 and 6 using either a ring-closing or an ene-yne metathesis without any loss of ee.