Abstract
A novel protocol for the asymmetric synthesis of 3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one is reported. Darzens condensation reactions of anisaldehyde with dichloroacetates, followed substitution reaction of sodium o-nitrophenylthiolate and bakers' yeast reduction furnished 2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylsulfanyl)-propionates. Further reduction of a nitro group and cyclization gave the title compound.
| Original language | English |
|---|---|
| Pages (from-to) | 147-151 |
| Number of pages | 5 |
| Journal | Heterocycles |
| Volume | 66 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - Dec 31 2005 |
ASJC Scopus subject areas
- Analytical Chemistry
- Pharmacology
- Organic Chemistry
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Komiyama, T., Takaguchi, Y., & Tsuboi, S. (2005). Novel protocol for the asymmetric synthesis of 3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one via bakers' yeast reduction. Heterocycles, 66(1), 147-151. https://doi.org/10.3987/COM-05-S(K)57