Development of Novel Guanidine–Bisurea Bifunctional Organocatalysts and their Application to Asymmetric α-Hydroxylation of Tetralone-derived β-Keto Esters

Minami Odagi; Kan Takayama; Kota Furukori; Tatsuya Watanabe; Kazuo Nagasawa

doi:10.1071/CH14144

RESEARCH ARTICLE

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Development of Novel Guanidine–Bisurea Bifunctional Organocatalysts and their Application to Asymmetric α-Hydroxylation of Tetralone-derived β-Keto Esters

Minami Odagi ^A , Kan Takayama ^A , Kota Furukori ^A , Tatsuya Watanabe ^A and Kazuo Nagasawa ^A ^B

+ Author Affiliations

- Author Affiliations

^A Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology, 2-24-16, Naka-cho, Koganei City, 184-8588 Tokyo, Japan.

^B Corresponding author. Email: knaga@cc.tuat.ac.jp

Australian Journal of Chemistry 67(7) 1017-1020 https://doi.org/10.1071/CH14144
Submitted: 13 March 2014 Accepted: 16 April 2014 Published: 28 May 2014

Abstract

A series of guanidine–bisurea bifunctional organocatalysts 4, with chiral centres located outside the urea groups, were synthesized. The novel catalyst 4 is conformationally more flexible than the original catalyst 1. In α-hydroxylation of tetralone- derived β-keto esters, 4 afforded the corresponding alcohols in high yields with moderate enantioselectivity.

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Development of Novel Guanidine–Bisurea Bifunctional Organocatalysts and their Application to Asymmetric α-Hydroxylation of Tetralone-derived β-Keto Esters

Abstract

References

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