Synthesis of new monodentate spiro phosphoramidite ligand and its application in Rh-catalyzed asymmetric hydrogenation reactions

Organic Letters
Shulin WuXumu Zhang

Abstract

[reaction: see text] A new spirocyclic diol, 9,9'-spirobixanthene-1,1'-diol, was synthesized in two steps from readily available starting material m-phenoxyanisole. Resolution of the racemic diol was achieved by cocrystallization with N-benzylcinchonidinium chloride and N-benzylquininium chloride in acetonitrile. The corresponding spiro monodentate phosphoramidite ligand has been prepared for Rh-catalyzed asymmetric hydrogenation of alpha-dehydroamino acid derivatives and itaconic acid with excellent enantioselectivities (up to >99% ee).

References

Jul 18, 2002·Chemical Communications : Chem Comm·Yu FuQi-Lin Zhou
Aug 14, 2003·Chemical Reviews·Wenjun Tang, Xumu Zhang
Jul 2, 2004·Organic Letters·Xu ChengQi-Lin Zhou

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Citations

Apr 30, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Pushkar ShejwalkarEike B Bauer
Mar 25, 2010·Angewandte Chemie·Johannes F Teichert, Ben L Feringa
Mar 29, 2006·Chemistry : a European Journal·Kuiling DingXisheng Wang
Feb 3, 2007·Organic & Biomolecular Chemistry·Weicheng ZhangXumu Zhang
Sep 5, 2008·Chemistry, an Asian Journal·Kuiling DingZheng Wang
Oct 6, 2007·Chemical Reviews·Carmen Najera, José M Sansano
Mar 29, 2020·Organic Letters·Weicong GuoJun Wang
Jul 24, 2018·Journal of the American Chemical Society·Zhiyao ZhengKuiling Ding
Jul 28, 2005·Journal of the American Chemical Society·Yan Liu, Kuiling Ding

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