Enantioselective Synthesis of Cyclic Amides and Amines through Mo-Catalyzed Asymmetric Ring-Closing Metathesis
Elizabeth S. Sattely, G. Alexander Cortez, David C. Moebius, Richard R. Schrock and Amir H. Hoveyda*
*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, Email: amir.hoveydabc.edu
E. S. Sattely, G. Alexander Cortez, D. C. Moebius, R. R. Schrock, A. H. Hoveyda, J. Am. Chem. Soc., 2005, 127, 8526-8533.
DOI: 10.1021/ja051330s (free Supporting Information)
Optically enriched N-fused bicyclic amides and small- and medium-ring unsaturated cyclic amines can be synthesized in up to 98% ee through Mo-catalyzed desymmetrization of readily available achiral polyene substrates. The effects of catalyst structure, olefin substitution, positioning of Lewis basic functional groups and ring size are examined and discussed in detail.
see article for more reactions