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  • Karlsson, Staffan, et al. (author)
  • Diastereoselective addition of chiral azomethine ylides to cyclic alpha,beta-unsaturated N-enoylbornanesultams
  • 2002
  • In: Journal of the Chemical Society. Perkin Transactions 1. - : Royal Society of Chemistry (RSC). - 1472-7781 .- 1364-5463. ; 2002:8, s. 1076-1081
  • Journal article (peer-reviewed)abstract
    • Doubly diastereoselective 1,3-dipolar cycloaddition reactions of chiral non-racemic azomethine ylides to cyclic five-and six-membered α,β-unsaturated N-enoylbornanesultams were carried out. When suitable solvents were used, the fused bicyclic adducts formed were obtained in good diastereoselectivity. Moreover, a change of the absolute configuration of the starting ylide precursor reversed the diastereoselectivity of some such reactions. Cleavage of the chiral auxiliary of the cycloadducts furnished amino alcohols and a β-amino ester. The latter was transformed into a known precursor of an antibacterial compound.
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Type of publication
journal article (1)
Type of content
peer-reviewed (1)
Author/Editor
Karlsson, Staffan (1)
Högberg, Hans-Erik (1)
University
Mid Sweden University (1)
Language
English (1)
Research subject (UKÄ/SCB)
Natural sciences (1)
Year

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