Asymmetric autocatalysis triggered by oxygen isotopically chiral glycerin.
نویسندگان
چکیده
Chiral (S)- and (R)-(18)O-glycerin induces enantioselective addition of diisopropylzinc to pyrimidine-5-carbaldehyde, and the subsequent asymmetric autocatalysis affords (R)- and (S)-pyrimidyl alkanol with high enantiomeric excess, respectively.
منابع مشابه
Asymmetric autocatalysis triggered by carbon isotope (13C/12C) chirality.
Many apparently achiral organic molecules on Earth may be chiral because of random substitution of the 1.11% naturally abundant 13C for 12C in an enantiotopic moiety within the structure. However, chirality from this source is experimentally difficult to discern because of the very small difference between 13C and 12C. We have demonstrated that this small difference can be amplified to an easil...
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Chiral isotactic polystyrenes induce the enantioselective addition of diisopropylzinc to pyrimidine-5-carbaldehyde, affording the enantiomerically enriched pyrimidyl alkanol with the corresponding absolute configuration to that of cryptochiral polystyrenes in conjunction with asymmetric autocatalysis.
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Mesoporous silica has been used as a heterogeneous support for catalysts; however, asymmetric induction by the helicity of inorganic mesoporous silica itself has not yet been achieved. P- and M-helical mesoporous silica was found to act as a chiral inorganic trigger for asymmetric autocatalysis to afford (S) and (R)-pyrimidyl alkanol with >99.5% ee, respectively.
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عنوان ژورنال:
- Organic & biomolecular chemistry
دوره 11 18 شماره
صفحات -
تاریخ انتشار 2013