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- Karlsson, Staffan, et al.
(författare)
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Diastereoselective addition of chiral azomethine ylides to cyclic alpha,beta-unsaturated N-enoylbornanesultams
- 2002
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Ingår i: Journal of the Chemical Society. Perkin Transactions 1. - : Royal Society of Chemistry (RSC). - 1472-7781 .- 1364-5463. ; 2002:8, s. 1076-1081
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Tidskriftsartikel (refereegranskat)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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