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 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
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. / Komiyama, Takuzo; Takaguchi, Yutaka; Tsuboi, Sadao.
In: Heterocycles, Vol. 66, No. 1, 31.12.2005, p. 147-151.Research output: Contribution to journal › Article
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TY - JOUR
T1 - 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
AU - Komiyama, Takuzo
AU - Takaguchi, Yutaka
AU - Tsuboi, Sadao
PY - 2005/12/31
Y1 - 2005/12/31
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=33646875725&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=33646875725&partnerID=8YFLogxK
U2 - 10.3987/COM-05-S(K)57
DO - 10.3987/COM-05-S(K)57
M3 - Article
AN - SCOPUS:33646875725
VL - 66
SP - 147
EP - 151
JO - Heterocycles
JF - Heterocycles
SN - 0385-5414
IS - 1
ER -