The diastereoselective allylation and reduction of camphor-derived α-ketoamides to give optically enriched α-hydroxyl amides with high to excellent stereoselectivities are described. Allylation was carried out using allyltributylstannane in the presence of a stoichiometric amount of a Lewis acid to afford the desired homoallylic alcohols in relatively high chemical yields (up to 98%) and stereoselectivities (up to 98% de). Diastereoselective reductions were performed with the relatively bulky hydride K-Selectride at -78°C to give the corresponding α-hydroxy amides in excellent chemical yields (up to 98%) and stereoselectivities (up to 98% de). The absolute configuration of the new stereogenic center of the major diastereomer was established by X-ray crystallographic analysis. Finally, stereochemical induction and the Lewis acid dependent reversal of stereoselectivity is described.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry
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Kulkarni, N. A. (Creator), Wang, S. (Creator), Lee, L. (Creator), Tsai, H. R. (Creator), Venkatesham, U. (Creator) & Chen, K. (Creator), Unknown Publisher, 2006
Wang, S. (Creator), Tsai, H. R. (Creator) & Chen, K. (Creator), Unknown Publisher, 2004
Kulkarni, N. A. (Contributor), Wang, S. (Contributor), Lee, L. (Contributor), Tsai, H. R. (Contributor), Venkatesham, U. (Contributor) & Chen, K. (Contributor), Unknown Publisher, 2006