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

Organic & Biomolecular Chemistry
Yusuke OhmaruMakoto Nakajima

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.

References

Aug 14, 2003·Chemical Reviews·Wenjun Tang, Xumu Zhang
Apr 8, 2004·Proceedings of the National Academy of Sciences of the United States of America·Andreas Pfaltz, William J Drury
Sep 9, 2005·Organic Letters·Carl A BusaccaChris H Senanayake
May 18, 2007·Accounts of Chemical Research·Weicheng ZhangXumu Zhang
Feb 1, 2008·Angewandte Chemie·Scott E Denmark, Gregory L Beutner
Jun 23, 2010·Organic & Biomolecular Chemistry·Maurizio Benaglia, Sergio Rossi
Jun 1, 2011·Chemistry : a European Journal·Yasushi ShimodaMakoto Nakajima
Feb 7, 2012·Organic & Biomolecular Chemistry·Simon Jones, Christopher J A Warner

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Citations

Jun 11, 2016·Journal of the American Chemical Society·Zhijian HuangYonggui Robin Chi
Apr 8, 2015·Organic & Biomolecular Chemistry·Wanfang Li, Xiao-Feng Wu
Feb 19, 2013·Angewandte Chemie·Yasushi ShimodaMakoto Nakajima
Oct 24, 2019·Chemical Reviews·Carmen NájeraMiguel Yus

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