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

7 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

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Allylation
Camphor
camphor
Stereoselectivity
amides
Lewis Acids
acids
Amides
hydrides
induction
alcohols
Acids
configurations
Hydrides
Hydroxyl Radical
Alcohols
x rays
X rays

ASJC Scopus subject areas

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

Cite this

Highly diastereoselective allylation and reduction of chiral camphor-derived α-ketoamides. / Kulkarni, Neelesh A.; Wang, Shy Guey; Lee, Li Chen; Tsai, Huei Ru; Venkatesham, Uppala; Chen, Kwunmin.

In: Tetrahedron Asymmetry, Vol. 17, No. 3, 06.02.2006, p. 336-346.

Research output: Contribution to journalArticle

Kulkarni, Neelesh A. ; Wang, Shy Guey ; Lee, Li Chen ; Tsai, Huei Ru ; Venkatesham, Uppala ; Chen, Kwunmin. / Highly diastereoselective allylation and reduction of chiral camphor-derived α-ketoamides. In: Tetrahedron Asymmetry. 2006 ; Vol. 17, No. 3. pp. 336-346.
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