Issue 23, 2012
From the journal:

Organic & Biomolecular Chemistry

Synthesis of aryl group-modified DIOP dioxides (Ar-DIOPOs) and their application as modular Lewis base catalysts†

Yusuke Ohmaru,a   Norimasa Sato,a   Makoto Mizutani,a   Shunsuke Kotani,b   Masaharu Sugiura*a  and  Makoto Nakajima*a  

* Corresponding authors

a Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Chuo-ku, Kumamoto 862-0973, Japan
E-mail: msugiura@kumamoto-u.ac.jp, nakajima@gpo.kumamoto-u.ac.jp

b Priority Organization for Innovation and Excellence, Kumamoto University, 5-1 Oe-honmachi, Chuo-ku, Kumamoto 862-0973, Japan

Abstract

Treatment of an optically pure tartaric acid-derived diiodide and various secondary phosphine oxides with LHMDS provides the corresponding aryl group-modified DIOP dioxides (Ar-DIOPOs). The activities of Ar-DIOPOs as Lewis base catalysts were investigated for several asymmetric transformations using chlorosilane reagents. The p-tolyl-substituted DIOPO (p-tolyl-DIOPO) was most effective for the reductive aldol reaction of chalcone and aldehydes with trichlorosilane, whereas the 2,8-dimethylphenoxaphosphine-derived DIOPO (DMPP-DIOPO) afforded the best enantioselectivity for the phosphonylation of conjugated aldehydes and the chlorinative aldol reaction of an ynone and benzaldehyde.

Graphical abstract: Synthesis of aryl group-modified DIOP dioxides (Ar-DIOPOs) and their application as modular Lewis base catalysts

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Article information

DOI
https://doi.org/10.1039/C2OB25338K
Article type
Paper
Submitted
16 Feb 2012
Accepted
16 Apr 2012
First published
17 Apr 2012

Org. Biomol. Chem., 2012,10, 4562-4570

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Synthesis of aryl group-modified DIOP dioxides (Ar-DIOPOs) and their application as modular Lewis base catalysts

Y. Ohmaru, N. Sato, M. Mizutani, S. Kotani, M. Sugiura and M. Nakajima, Org. Biomol. Chem., 2012, 10, 4562 DOI: 10.1039/C2OB25338K

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