Diastereoselective addition of chiral azomethine ylides to cyclic alpha,beta-unsaturated N-enoylbornanesultams

Karlsson, StaffanMittuniversitetet,Institutionen för naturvetenskap (-2008) (author)

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.

Högberg, Hans-ErikMittuniversitetet,Institutionen för naturvetenskap (-2008)(Swepub:miun)hansho (author)
MittuniversitetetInstitutionen för naturvetenskap (-2008) (creator_code:org_t)

In:Journal of the Chemical Society. Perkin Transactions 1: Royal Society of Chemistry (RSC)2002:8, s. 1076-10811472-77811364-5463

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