Issue 31, 2014
From the journal:

Organic & Biomolecular Chemistry

Asymmetric organocatalytic desymmetrization of 4,4-disubstituted cyclohexadienones at high pressure: a new powerful strategy for the synthesis of highly congested chiral cyclohexenones†

Naomu Miyamae,a   Naruhisa Watanabe,a   Maya Moritaka,a   Keiji Nakano,a   Yoshiyasu Ichikawaa  and  Hiyoshizo Kotsuki*a  

* Corresponding authors

a Laboratory of Natural Products Chemistry, Faculty of Science, Kochi University, Akebono-cho, Kochi 780-8520, Japan
E-mail: kotsuki@kochi-u.ac.jp

Abstract

A highly diastereoselective and enantioselective method for the asymmetric desymmetrization of 4,4-disubstituted cyclohexadienones using the Michael addition reaction of malonates under catalysis with the primary amine–thiourea conjugate catalyst and PPY at high pressure was developed.

Graphical abstract: Asymmetric organocatalytic desymmetrization of 4,4-disubstituted cyclohexadienones at high pressure: a new powerful strategy for the synthesis of highly congested chiral cyclohexenones

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Article information

DOI
https://doi.org/10.1039/C4OB00733F
Article type
Paper
Submitted
07 Apr 2014
Accepted
14 May 2014
First published
14 May 2014

Org. Biomol. Chem., 2014,12, 5847-5855

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Asymmetric organocatalytic desymmetrization of 4,4-disubstituted cyclohexadienones at high pressure: a new powerful strategy for the synthesis of highly congested chiral cyclohexenones

N. Miyamae, N. Watanabe, M. Moritaka, K. Nakano, Y. Ichikawa and H. Kotsuki, Org. Biomol. Chem., 2014, 12, 5847 DOI: 10.1039/C4OB00733F

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