1023920-77-5Relevant academic research and scientific papers
Sharpless asymmetric dihydroxylation as the key step in the enantioselective synthesis of spirocyclic σ1 receptor ligands
Holl, Katharina,Schepmann, Dirk,Daniliuc, Constantin Gabriel,Wuensch, Bernhard
, p. 268 - 277 (2014/03/21)
The enantioselective synthesis of fluorinated spirocyclic σ1 ligands involved three key steps: (1) the Sharpless asymmetric dihydroxylation of 2-bromostyrene 5 provided enantiomerically pure diols (R)-6 and (S)-6 establishing the stereogenic center; (2) the intramolecular opening of the oxirane ring of (R)-11 and (S)-11, which occurred with excellent regioselectivity and complete inversion of configuration giving access to enantiomerically pure alcohols (S)-7a and (R)-7a; (3) the treatment of alcohols (S)-7b and (R)-7b with DAST, which led to the fluoromethyl derivatives (S)-1 and (R)-1 without racemization. X-ray crystal structure analysis of the tosylate (R)-13 confirmed the absolute configuration of the spirocyclic compounds as well as the enantioselectivity during the Sharpless asymmetric dihydroxylation of 5. The (S)-configured fluoromethyl derivative (S)-1 revealed a high σ1 affinity (Ki = 1.8 nM), high eudismic ratio (factor 8) and high selectivity over the σ2 subtype (667-fold).
Enantioselective synthesis of 1-arylethanediols by rhodium-catalyzed transfer hydrogenation of α-tosyloxyarylketones
Lee, Do-Min,Kumaraswamy, Gullapalli,Lee, Kee-In
experimental part, p. 73 - 78 (2010/03/26)
Catalytic transfer hydrogenation of α-tosyloxyarylketones mediated by a chiral rhodium complex using an azeotropic mixture of formic acid/triethylamine afforded the corresponding 1-arylethanediol monotosylates in excellent yield with high enantioselectivity.
METHOD FOR THE PREPARATION OF OPTICALLY ACTIVE 2-SULFONYLOXY-1-PHENYLETHANOL DERIVATIVES
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Page/Page column 17, (2008/12/05)
Optically active 2-sulfonyloxy-1-phenylethanol derivative of formula (II) can be prepared easily and selectively by the method of the present invention using an asymmetric reduction of an α-sulfonyloxy acetophenone compound with a rhodium catalyst having petamethylcyclopentadienyl group and a hydrogen donor, and the compound of formula (II) obtained in the inventive method exhibits a higher e.e. (enantiomer excess) value than that of the products in the conventional methods.
