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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)


Abstract

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.

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Key Words

Cyclic Amines, Cyclic Amides, Ring Closing Metathesis


ID: J48-Y2005-2400