Issue 32, 2013
From the journal:

Organic & Biomolecular Chemistry

Catalytic highly asymmetric 1,5(6)-selective cyclization reaction of α-hydroxyimino cyclic ketones: direct approach to ring-fused hydroxyimino dihydropyrans†

Luping Liu,‡a   Dekui Zhang,‡abc   Panpan Zhang,a   Xianxing Jiang*a  and  Rui Wang*a  

* Corresponding authors

a Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Institute of Biochemistry and Molecular Biology, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, China
E-mail: wangrui@lzu.edu.cn, xianxingjiang@gmail.com

b Department of Gastroenterology, the Second Hospital of Lanzhou University, Lanzhou University, Lanzhou 730000, China

c Department Molecular and Medical Pharmacology, David Geffen School of Medicine, University of California, Los Angeles, CA 90095, USA

Abstract

Herein, we have disclosed a catalytic asymmetric 1,5(6)-selective Michael/cyclization reaction of α-hydroxyimino cyclic ketones with γ,β-unsaturated α-keto esters. Unlike the previous catalytic strategies, this reaction provides a convenient 1,5(6)-selective asymmetric pathway to access synthetically useful ring-fused dihydropyrans. In general, high levels of yield, enantio- and diastereoselectivity (up to 99% yield, >99% ee and >20 : 1 dr) were obtained.

Graphical abstract: Catalytic highly asymmetric 1,5(6)-selective cyclization reaction of α-hydroxyimino cyclic ketones: direct approach to ring-fused hydroxyimino dihydropyrans

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Article information

DOI
https://doi.org/10.1039/C3OB41001C
Article type
Communication
Submitted
13 May 2013
Accepted
18 Jun 2013
First published
19 Jun 2013

Org. Biomol. Chem., 2013,11, 5222-5225

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Catalytic highly asymmetric 1,5(6)-selective cyclization reaction of α-hydroxyimino cyclic ketones: direct approach to ring-fused hydroxyimino dihydropyrans

L. Liu, D. Zhang, P. Zhang, X. Jiang and R. Wang, Org. Biomol. Chem., 2013, 11, 5222 DOI: 10.1039/C3OB41001C

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