1106677-07-9Relevant academic research and scientific papers
Design of thermally stable versions of the burgess reagent: Stability and reactivity study (1)
Metcalf, Thomas A.,Simionescu, Razvan,Hudlicky, Tomas
supporting information; experimental part, p. 3447 - 3450 (2010/07/07)
Three new versions of the Burgess reagent were synthesized and their thermal stability investigated by NMR. The new reagents exhibited improved reactivity toward epoxides, diols, and vinyl oxiranes as compared with the original version.
New options for the reactivity of the burgess reagent with epoxides in both racemic and chiral auxiliary modes - Structural and mechanistic revisions, computational studies, and application to synthesis
Leisch, Hannes,Sullivan, Bradford,Fonovic, Branden,Dudding, Travis,Hudlicky, Tomas
experimental part, p. 2806 - 2819 (2009/09/25)
The reaction of the chiral auxiliary version of the Burgess reagent with epoxides yields diastereomeric pairs of sulfamldates, which, lead, to cis and trans amino alcohols in each, enantiomeric series. Experimental and spectral, details are provided for a
Formal total synthesis of (-)- and (+)-balanol: two complementary enantiodivergent routes from vinyloxiranes and vinylaziridines
Gilmet, Jacqueline,Sullivan, Bradford,Hudlicky, Tomas
body text, p. 212 - 220 (2009/04/06)
Formal total syntheses of both enantiomers of balanol have been achieved by the preparation of the protected hexahydroazepine core 2. Two complementary routes have been investigated. The first relied on the regioselective opening of 1,2-epoxycyclohex-3-ene with a chiral-auxiliary version of the Burgess reagent to provide a diastereomeric pair of cis-fused cyclic sulfamidates. The sulfamidates were transformed to trans-amino benzoates with ammonium benzoate and, after separation, converted to (-)-2 and (+)-2 by oxidative cleavage and reductive amination. The second approach utilized vinylaziridines derived from 1-bromo-2,3-dihydroxycyclohexa-4,6-diene obtained by the whole-cell fermentation of bromobenzene with Escherichia coli JM109(pDTG601). Stereoselective opening of the aziridines generated the requisite trans-amino alcohol derivatives, which after saturation of the vinyl bromide moieties were converted to (-)-2 and (+)-2 by oxidative cleavage of the cis-diol and reductive amination. Experimental and spectral data are provided for all new compounds.
