221001-47-4Relevant academic research and scientific papers
Reagent-controlled asymmetric homologation of boronic esters by enantioenriched main-group chiral carbenoids
Blakemore, Paul R.,Marsden, Stephen P.,Vater, Huw D.
, p. 773 - 776 (2007/10/03)
Putative enantioenriched carbenoid species, (R)-1-chloro-2- phenylethylmagnesium chloride (9) and (S)-1-chloro-2-phenylethyllithium (26), generated in situ by sulfoxide ligand exchange from (-)-(Rs,R)-1- chloro-2-phenylethyl p-tolyl sulfoxide (8), effected the stereocontrolled homologation of boronic esters. sec-Alcohols derived from the product boronates by oxidation with basic hydrogen peroxide exhibited % ee closely approaching that of sulfoxide 8 in examples employing Li-carbenoid 26.
Highly enantiomerically enriched α-haloalkyl grignard reagents
Hoffmann, Reinhard W.,Nell, Peter G.,Leo, Roland,Harms, Klaus
, p. 3359 - 3365 (2007/10/03)
α-Chloro- and α-bromoalkyl Grignard reagents 11 and 30 with > 97% ee (enantiomeric excess) were generated by a sulfoxide/magnesium exchange reaction from the enantiomerically and diastereomerically pure sulfoxides 25 and 27. The resulting α-haloalkyl Grig
α-Chloroalkylmagnesium reagents of >90% ee by sulfoxide/magnesium exchange
Hoffmann, Reinhard W.,Nell, Peter G.
, p. 338 - 340 (2007/10/03)
Not only for ligand exchange at sulfoxides can the sulfoxide/magnesium exchange reaction be used, but it also provides a possibility to generate Grignard reagents in way that avoids metallic magnesium and thus radical processes. Therefore, enantiomerically pure Grignard reagents can be obtained from the corresponding sulfoxides [Eq. (a)].
