Effective and novel enantioselective preparation of pyranopyrazoles and pyranocoumarins that is catalyzed by a quinine-derived primary amine

Sai Yang; Liu-lan Shen; Yoon-Jung Kim; Jin-Hyun Jeong

doi:10.1039/C5OB01656H

Effective and novel enantioselective preparation of pyranopyrazoles and pyranocoumarins that is catalyzed by a quinine-derived primary amine

Sai Yang,^a Liu-lan Shen,^a Yoon-Jung Kim^a and Jin-Hyun Jeong*^a

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* Corresponding authors

^a College of Pharmacy and Yonsei Institute of Pharmaceutical Sciences, Yonsei University, 85 Songdogwahak-ro, Yeonsu-gu, Incheon 406-840, Republic of Korea
E-mail: organicjeong@yonsei.ac.kr
Fax: +82 32 749 4105
Tel: +82 32 749 4509

Abstract

In this study, we executed an effective and novel enantioselective Michael/cyclodehydration sequential reaction between pyrazolin-5-one (or 4-hydroxy-2-pyrone) and chalcones that is catalyzed by a quinine-derived primary amine L7 in the presence of Boc-D-Phg-OH. Chiral pyranopyrazoles and pyranocoumarins were obtained in excellent enantioselectivities (up to 93%) with moderate yields and moderate enantioselectivities with high yields (up to 84%).

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Publication details

The article was received on 07 Aug 2015, accepted on 28 Oct 2015 and first published on 28 Oct 2015

Article type: Paper

DOI: 10.1039/C5OB01656H

Author version available: Download Author version (PDF)

Citation: Org. Biomol. Chem., 2016,14, 623-630

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Effective and novel enantioselective preparation of pyranopyrazoles and pyranocoumarins that is catalyzed by a quinine-derived primary amine

S. Yang, L. Shen, Y. Kim and J. Jeong, Org. Biomol. Chem., 2016, 14, 623
DOI: 10.1039/C5OB01656H
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Organic & Biomolecular Chemistry

Effective and novel enantioselective preparation of pyranopyrazoles and pyranocoumarins that is catalyzed by a quinine-derived primary amine

Abstract

Supplementary files

Publication details

Effective and novel enantioselective preparation of pyranopyrazoles and pyranocoumarins that is catalyzed by a quinine-derived primary amine

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