Asymmetric Organocatalytic Efficiency of Synthesized Chiral ?-Amino Alcohols in Ring-Opening of Glycidol with Phenols
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Tarih
2012
Yazarlar
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Springer
Erişim Hakkı
info:eu-repo/semantics/closedAccess
Özet
A series of novel chiral beta-amino alcohols 3-5 and 7-10 were synthesized by regioselective ring opening of epoxides and chiral amines with a straightforward method in high yields (up to 99 %). Kinetic resolution of racemic glycidol with phenols was achieved by using chiral amino alcohols as organocatalysts. Amino alcohols 5, 8 and 10 exhibited the highest enantioselectivities with p-cresol, phenol, and p-methoxyphenol by 63, 65, 58 % ee, respectively. The moderate enantioselectivities were observed with catalyst 9b towards all the nucleophiles (34-48 % ee). The ee values of the desired 3-aryloxy-1,2-diols were determined by HPLC. This study presents an attractive tool for the synthesis of beta-blockers and structurally complex molecules.
Açıklama
Anahtar Kelimeler
Epoxide Ring Opening, Beta-Amino Alcohols, Kinetic Resolution, Organocatalysts, 3-Aryloxy-1,2-Propanediols
Kaynak
Catalysis Letters
WoS Q Değeri
Q2
Scopus Q Değeri
Q2
Cilt
142
Sayı
6
