Abstract
A reversal in enantioselectivity was observed by the combination of a chiral diol and achiral alcohols as a chiral initiator in the asymmetric alkylation of a pyrimidine-5-carbaldehyde using diisopropylzinc. (2S,3S)-Butane-2,3-diol alone induced (R)-pyrimidyl alkanol, while a mixture of the chiral diol and phenol derivatives induced (S)-pyrimidyl alkanol. The effect of achiral alcohols is also discussed.
| Original language | English |
|---|---|
| Pages (from-to) | 1023-1027 |
| Number of pages | 5 |
| Journal | Tetrahedron Asymmetry |
| Volume | 23 |
| Issue number | 14 |
| DOIs | |
| Publication status | Published - 2012 Jul 31 |
ASJC Scopus subject areas
- Catalysis
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry
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Shibata, T., Tarumi, H., Kawasaki, T., & Soai, K. (2012). Reversal in enantioselectivity induced by achiral alcohols in asymmetric autocatalysis in the presence of a chiral diol as a chiral initiator. Tetrahedron Asymmetry, 23(14), 1023-1027. https://doi.org/10.1016/j.tetasy.2012.07.010