102817-15-2Relevant academic research and scientific papers
Preparation of enantiomerically enriched bromohydrins from [N-(p-tolylsulfonyl)sulfoximino]oxiranes using in situ reduction of α-bromo aldehydes
Bailey, Peter L.,Briggs, Andrew D.,Jackson, Richard F. W.,Pietruszka, Joerg
, p. 3359 - 3363 (2007/10/03)
Treatment of enantiomerically pure [N-(p-tolylsulfonyl)sulfoximino]oxiranes 6 with MgBr2 in the presence of tetrabutylammonium borohydride gives enantiomerically enriched bromohydrins 3, together with small amounts of the primary alcohols 11. The bromohydrins 3 are isolated in good yields with enantiomeric excesses in the range 70% to 91%. This process establishes that α-bromo aldehydes have sufficient configurational stability to be viable synthetic intermediates.
STEREOSELECTIVE SYNTHESIS OF ENANTIOMERICALLY PURE 1-(E)-ALKENYLSULFOXIMINES
Erdelmeier, Irene,Gais, Hans-Joachim
, p. 4359 - 4362 (2007/10/02)
Optically active (E)-N-tosyl-S-(1-alkenyl)-S-phenylsulfoximines 4 are synthesized stereoselectively in a one pot sequence from readily available 1 via C-silylation, metallation and reaction of the corresponding lithiosulfoximine 3 with various carbonyl compounds.The E1-MS spectra of the so prepared alkenylsulfoximines 4 show unexpected fragmentations, pointing to a new, unusual S-O-migration of the 1-alkenyl moiety.
