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Issue 23, 2012
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Synthesis of aryl group-modified DIOP dioxides (Ar-DIOPOs) and their application as modular Lewis base catalysts

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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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Publication details

The article was received on 16 Feb 2012, accepted on 16 Apr 2012 and first published on 17 Apr 2012


Article type: Paper
DOI: 10.1039/C2OB25338K
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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