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Paper | Regular issue | Vol 53, No. 3, 2000, pp.637-655
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8805
Studies on the Rh(II)-catalyzed C-H Insertion Reaction of Some Derivatives of N-[4-{(S)-1,2-Dihydroxy- butyl}]-α-diazoanilides: Site-Selectivity

Andrew G. H. Wee* and Douglas D. McLeod

*Department of Chemistry, University of Regina, Regina, Saskatchewan, S4S 0A2, Canada


The Rh(II)-catalyzed reactions of diazoamides (la, c-e) were investigated. The results show that both steric and electronic effects work in concert to govern the regio- and chemo-selectivity of the reaction. The diastereoselectivity of the reaction in the formation of 5a was determined to be 74% de and the sense of 1,2-induction was found to be S at the newly formed C-4 stereogenic centre.