446
N. Paul
Fig. 1 A model structure of diastereotopic TS produced by Re-facial approach of epoxidating
oxygen
resolution. Electron-releasing effect of alkyl group is supposed to be one feature for
its selectivity. More space-filling group strongly imposes a geometrical constraint
which siphones (E,R) alcohol more towards epoxide.
3.5 Justification of Scheme 1 by Model TS Structure
The discussion covered in this section considers allyl alcohol as starting compound
in which carbon-bearing alcoholic hydroxylic group is a chiral centre and adjacent double-bonded carbon is a prochiral carbon. The product spread obtained from
Scheme 1 is represented in Table 2.
The model based on stochiometry ratio of reacting components clearly illustrates
dimeric structure of catalyst. Attachment of chiral auxiliary allows trans coordination of substrate through alcoholic oxygen and oxidant peroxide. Chiral auxiliary
when change from diethyl tartrate to diisopropyl tartrate, stereoelectronic factor of
isopropyl group offers a stringent action on catalyst–substrate–epoxidating agent
aggregate. And trans orientation of substrate–oxidant arrangement hardly allows
N. Paul
Fig. 1 A model structure of diastereotopic TS produced by Re-facial approach of epoxidating
oxygen
resolution. Electron-releasing effect of alkyl group is supposed to be one feature for
its selectivity. More space-filling group strongly imposes a geometrical constraint
which siphones (E,R) alcohol more towards epoxide.
3.5 Justification of Scheme 1 by Model TS Structure
The discussion covered in this section considers allyl alcohol as starting compound
in which carbon-bearing alcoholic hydroxylic group is a chiral centre and adjacent double-bonded carbon is a prochiral carbon. The product spread obtained from
Scheme 1 is represented in Table 2.
The model based on stochiometry ratio of reacting components clearly illustrates
dimeric structure of catalyst. Attachment of chiral auxiliary allows trans coordination of substrate through alcoholic oxygen and oxidant peroxide. Chiral auxiliary
when change from diethyl tartrate to diisopropyl tartrate, stereoelectronic factor of
isopropyl group offers a stringent action on catalyst–substrate–epoxidating agent
aggregate. And trans orientation of substrate–oxidant arrangement hardly allows