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Molecules 2015, 20(7), 12590-12598; doi:10.3390/molecules200712590

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

1
Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology, 2-24-16, Naka-cho, Koganei city, 184-8588 Tokyo, Japan
2
Department of Chemistry, Faculty of Science, Rikkyo University, 3-34-1, Nishi-Ikebukuro, Toshima-ku, 171-8501 Tokyo, Japan
*
Author to whom correspondence should be addressed.
Academic Editor: Choon-Hong Tan
Received: 5 June 2015 / Revised: 5 July 2015 / Accepted: 6 July 2015 / Published: 10 July 2015
(This article belongs to the Special Issue Brønsted Base Catalysis in Organic Synthesis)
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Abstract

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. View Full-Text
Keywords: guanidine; urea; organocatalyst; α-hydroxylation guanidine; urea; organocatalyst; α-hydroxylation
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Odagi, M.; Takayama, K.; Sato, M.; Yamanaka, M.; Nagasawa, K. Development of Guanidine-Bisurea Bifunctional Organocatalysts with a Chiral Pyrrolidine Moiety and Application to α-Hydroxylation of Tetralone-Derived β-Keto Esters. Molecules 2015, 20, 12590-12598.

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