- Synthesis of enantiomerically pure (R)-and (S)-1-benzoyloxypropane-2,3-diol and revision of the stereochemical outcome of the Candida antarctica lipase-catalyzed benzoylation of glycerol
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Enantiomerically pure (R)- and (S)-1-benzoyloxypropane-2,3-diol have been prepared from (S)-(+)-2,2-dimethyl-1,3-dioxolane-4-methanol and used as reference compounds to correct the reported stereochemical outcome of the Candida antarctica lipase (CAL)-cat
- Casati, Silvana,Ciuffreda, Pierangela,Santaniello, Enzo
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p. 658 - 661
(2011/07/08)
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- Chiral Lactols, XI. - A Method for the Determination of the Absolute Configuration of Chiral Alkanols
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Chiral secondary alcohols which are protected with the enantiomerically pure lactol 1 or 2 show significant differences in 13C-chemical shifts around the glycosidic linkage.An easy method for determination of the absolute configuration of secondary alcoho
- Noe, Christian R.,Knollmueller, Max,Miculka, Christian,Dungler, Karin,Wagner, Ernst,Ettmayer, Peter
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p. 887 - 892
(2007/10/02)
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- NUCLEOPHILIC DISPLACEMENT REACTIONS OF THE METHANESULFONATES OF THE 1-O-BENZOYL-1,2-, -1,3-, AND -1,4-GLYCOLS
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Nucleophilic displacement reactions of the methanesulfonates (8a-c) of the 1-O-benzoyl-1,2-, -1,3-, and -1,4-glycols (7a-c) with potassium acetate in boiling acetic anhydride have been examined.Both benzoyloxy-group participation pathway (path A) and SN2 displacement pathway (path B) have been involved in the 1,2-(8a)- and 1,3-(8b)-substrates to give a mixture of the primary (10a,b) and the secondary (11a,b) acetates with complete inversion of chiralities.On the other hand, only SN2 displacement pathway (path B) has been involved in the 1,4-substrate (8c) to give the secondary acetate (11c) with inversion of the chirality.
- Takano, Seiichi,Hirama, Michiyasu,Seya, Kazuhiko,Ogasawara, Kunio
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p. 4233 - 4236
(2007/10/02)
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