Asymmetric Epoxidation of α-Substituted Acroleins Catalyzed by Diphenylprolinol Silyl Ether
Abstract
Asymmetric epoxidation of α-substituted acroleins with hydrogen peroxide has been catalyzed by diphenylprolinol diphenylmethylsilyl ether to afford α-substituted-β,β-unsubstituted-α,β-epoxy aldehyde with excellent enantioselectivity and the generation of a chiral quaternary carbon center. The method was applied to a short synthesis of (R)-methyl palmoxirate.
Keywords:
epoxidation / Asymmetric epoxidation / (R)-methyl palmoxirateSource:
Organic Letters, 2010, 12, 23, 5434-5437Publisher:
- American Chemical Society (ACS)
DOI: 10.1021/ol102269s
ISSN: 1523-7060
PubMed: 21049980
Scopus: 2-s2.0-78650339798
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IHTMTY - JOUR AU - Bondžić, Bojan AU - Urushima, Tatsuya AU - Ishikawa, Hayato AU - Hayashi, Yujiro PY - 2010 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/6812 AB - Asymmetric epoxidation of α-substituted acroleins with hydrogen peroxide has been catalyzed by diphenylprolinol diphenylmethylsilyl ether to afford α-substituted-β,β-unsubstituted-α,β-epoxy aldehyde with excellent enantioselectivity and the generation of a chiral quaternary carbon center. The method was applied to a short synthesis of (R)-methyl palmoxirate. PB - American Chemical Society (ACS) T2 - Organic Letters T1 - Asymmetric Epoxidation of α-Substituted Acroleins Catalyzed by Diphenylprolinol Silyl Ether VL - 12 IS - 23 SP - 5434 EP - 5437 DO - 10.1021/ol102269s ER -
@article{ author = "Bondžić, Bojan and Urushima, Tatsuya and Ishikawa, Hayato and Hayashi, Yujiro", year = "2010", abstract = "Asymmetric epoxidation of α-substituted acroleins with hydrogen peroxide has been catalyzed by diphenylprolinol diphenylmethylsilyl ether to afford α-substituted-β,β-unsubstituted-α,β-epoxy aldehyde with excellent enantioselectivity and the generation of a chiral quaternary carbon center. The method was applied to a short synthesis of (R)-methyl palmoxirate.", publisher = "American Chemical Society (ACS)", journal = "Organic Letters", title = "Asymmetric Epoxidation of α-Substituted Acroleins Catalyzed by Diphenylprolinol Silyl Ether", volume = "12", number = "23", pages = "5434-5437", doi = "10.1021/ol102269s" }
Bondžić, B., Urushima, T., Ishikawa, H.,& Hayashi, Y.. (2010). Asymmetric Epoxidation of α-Substituted Acroleins Catalyzed by Diphenylprolinol Silyl Ether. in Organic Letters American Chemical Society (ACS)., 12(23), 5434-5437. https://doi.org/10.1021/ol102269s
Bondžić B, Urushima T, Ishikawa H, Hayashi Y. Asymmetric Epoxidation of α-Substituted Acroleins Catalyzed by Diphenylprolinol Silyl Ether. in Organic Letters. 2010;12(23):5434-5437. doi:10.1021/ol102269s .
Bondžić, Bojan, Urushima, Tatsuya, Ishikawa, Hayato, Hayashi, Yujiro, "Asymmetric Epoxidation of α-Substituted Acroleins Catalyzed by Diphenylprolinol Silyl Ether" in Organic Letters, 12, no. 23 (2010):5434-5437, https://doi.org/10.1021/ol102269s . .