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Stereoselective Lewis Acid-Catalyzed α-Acylvinyl Additions

Troy E. Reynolds, Ashwin R. Bharadwaj and Karl A. Scheidt*

*Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, Email:

T. E. Reynolds, A. R. Bharadwaj, K. A. Scheidt, J. Am. Chem. Soc., 2006, 128, 15382-15383.

DOI: 10.1021/ja0653674 (free Supporting Information)

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Silyloxyallenes derived from α-hydroxypropargylsilanes add efficiently to aldehydes with catalytic amounts of Lewis acids. The allenes are accessed from the corresponding propargylsilanes in a base-catalyzed 1,2-Brook rearrangement/SE2' process. Conversion to the silyloxyallenes occurs with minimal erosion in optical activity.

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N-Heterocyclic Carbene-Initiated α-Acylvinyl Anion Reactivity: Additions of α-Hydroxypropargylsilanes to Aldehydes

T. E. Reynolds, C. A. Stern, K. A. Scheidt, Org. Lett., 2007, 9, 2581-2584.

Key Words

Baylis-Hillman adducts

ID: J48-Y2006-3910