Issue 8, 2006
From the journal:

Chemical Communications

Intramolecular bromo-amination of 1,4-cyclohexadieneaminal: one-pot discrimination of two olefins and concise asymmetric synthesis of (−)-γ-lycorane†

Hiromichi Fujioka,*a   Kenichi Murai,a   Yusuke Ohba,a   Hideki Hirosea  and  Yasuyuki Kita*a  

* Corresponding authors

a Graduate School of Pharmaceutical Sciences, Osaka University, 1-6, Yamada-oka, Suita, Osaka, Japan
E-mail: fujioka@phs.osaka-u.ac.jp; kita@phs.osaka-u.ac.jp

Abstract

The reaction of cyclohexa-2,5-dienyl-1-methylaldehyde and optically pure 1,2-diaryl-1,2-diamine followed by intramolecular bromo-amination produced a one-pot discrimination of two olefins in the cyclohexane system, which was used for the asymmetric synthesis of (−)-γ-lycorane.

Graphical abstract: Intramolecular bromo-amination of 1,4-cyclohexadiene aminal: one-pot discrimination of two olefins and concise asymmetric synthesis of (−)-γ-lycorane

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Article information

DOI
https://doi.org/10.1039/B512161B
Article type
Communication
Submitted
30 Aug 2005
Accepted
17 Nov 2005
First published
29 Nov 2005

Chem. Commun., 2006, 832-834

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Intramolecular bromo-amination of 1,4-cyclohexadiene aminal: one-pot discrimination of two olefins and concise asymmetric synthesis of (−)-γ-lycorane

H. Fujioka, K. Murai, Y. Ohba, H. Hirose and Y. Kita, Chem. Commun., 2006, 832 DOI: 10.1039/B512161B

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