153683-50-2Relevant academic research and scientific papers
Preparation of enantiomerically enriched bromohydrins by reaction of sulfoximinooxiranes with MgBr2 in the presence of tetra-butylammonium borohydride
Bailey, Peter L.,Briggs, Andrew D.,Jackson, Richard F. W.,Pietruszka, Joerg
, p. 6611 - 6614 (1993)
Treatment of enantiomerically pure N-tosylsulfoximinooxiranes 6 with MgBr2 in the presence of tetra-butylammonium borohydride gives enantiomerically enriched bromohydrins 3, together with small amounts of the simple primary alcohols. The bromohydrins are isolated in good yields with enantiomeric excess in the range 70% to 91 % (as assessed by enantioselective g.l.c.
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.
