Development of Guanidine-Bisurea Bifunctional Organocatalysts with a Chiral Pyrrolidine Moiety and Application to α-Hydroxylation of Tetralone-Derived β-Keto Esters

Molecules

Minami Odagi¹  Kan Takayama¹  Makoto Sato²  Masahiro Yamanaka²  Kazuo Nagasawa¹ 

[1] Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology, 2-24-16, Naka-cho, Koganei city, 184-8588 Tokyo, Japan; E-Mails:;Department of Chemistry, Faculty of Science, Rikkyo University, 3-34-1, Nishi-Ikebukuro, Toshima-ku, 171-8501 Tokyo, Japan; E-Mails:

关键词: guanidine;    urea;    organocatalyst;    α-hydroxylation;   

DOI  :  10.3390/molecules200712590

来源: mdpi

【 摘 要 】

Novel guanidine-bisurea bifunctional organocatalysts 5 bearing a chiral pyrrolidine moiety on guanidine were designed with the guidance of DFT calculations. The resulting organocatalysts 5 were examined for α-hydroxylation of tetralone-derived β-keto esters, and good selectivity was obtained with 5j bearing a methoxymethyl ether-containing chiral pyrrolidine moiety.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.