Highly diastereoselective allylation and reduction of chiral camphor-derived α-ketoamides

Neelesh A. Kulkarni, Shy Guey Wang, Li Chen Lee, Huei Ru Tsai, Uppala Venkatesham, Kwunmin Chen

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)336-346
Number of pages11
JournalTetrahedron Asymmetry
Volume17
Issue number3
DOIs
Publication statusPublished - 2006 Feb 6

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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