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Asymmetric Autocatalysis of a Pyrimidyl Alkanol Induced by Chiral Monosubstituted [2.2]Paracyclophanes
β Scribed by Tanji, Shigehisa; Ohno, Atsushi; Sato, Itaru; Soai, Kenso
- Book ID
- 127030664
- Publisher
- American Chemical Society
- Year
- 2001
- Tongue
- English
- Weight
- 38 KB
- Volume
- 3
- Category
- Article
- ISSN
- 1523-7060
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π SIMILAR VOLUMES
Experimental and kinetic analysis of asymmetric autocatalysis with amplification of ee in the enantioselective addition of diisopropylzinc to 2-alkynylpyrimidine-5-carbaldehyde using chiral 2-alkynyl-5-pyrimidyl alkanol with low ee's are described.
Enantiomerically enriched pyrimidyl alkanol with either S or R configuration was obtained stochastically from the reaction between pyrimidine-5-carbaldehyde and diisopropylzinc without adding chiral substances in conjunction with subsequent asymmetric autocatalysis, leading to amplification of the e
The synthesis of enantiomerically pure (S)-4-formyl-[2.2]paracyclophane 1 (>99% ee) and (R)-4-hydroxymethyl-[2.2]paracyclophane 2 (>78% ee) was achieved by bioreduction of (RS)-I with a yield of 49 and 34% respectively. From several microorganisms screened only a strain of the yeast Saccharomyces ce