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Kwon Group – Professor Product Portal

Professor Ohyun Kwon

Professor Ohyun Kwon

The Kwon Group has made major strides in the development and application of nucleophilic phosphinocatalysis reactions as a means to synthesize carbo- and heterocycles that serve as synthetic intermediates for both natural products and medicinally useful compounds. Although soft-nucleophilic phosphinocatalysis has been known since the 1960s, not until the 2000s did the area of phosphinocatalysis begin its explosive growth. With the discovery and exploitation of new chemical reactivity, the Kwon Group’s research has thus helped to pioneer the phosphinocatalysis as one of the chief areas of organocatalysis research.

To facilitate phosphinocatalysis reactions in an enantioselective fashion, the Kwon Group has developed a simple protocol for preparing a new class of rigid [2.2.1] bicyclic chiral phosphines from naturally occurring trans-4-hydroxy-L-proline. This efficient, modular synthesis has allowed 12 different [2.2.1] bicyclic chiral phosphines to be made commercially available from us. Along with their synthetic utility in nucleophilic organocatalysis, as demonstrated in two articles (in JACS and Chem. Sci., respectively), these electron-rich monodentate P-chiral phosphines might be useful in asymmetric transition metal catalysis.

Kwon Group Website

Recent papers from the Kwon Group

1.
Henry CE, Xu Q, Fan YC, Martin TJ, Belding L, Dudding T, Kwon O. 2014. Hydroxyproline-Derived Pseudoenantiomeric [2.2.1] Bicyclic Phosphines: Asymmetric Synthesis of (+)- and (?)-Pyrrolines. J. Am. Chem. Soc.. 136(34):11890-11893. http://dx.doi.org/10.1021/ja505592h
2.
Andrews IP, Kwon O. 2012. Enantioselective total synthesis of (+)-ibophyllidine via an asymmetric phosphine-catalyzed [3 + 2] annulation. Chem. Sci.. 3(8):2510. http://dx.doi.org/10.1039/c2sc20468a
3.
Fan YC, Kwon O. 2013. Advances in nucleophilic phosphine catalysis of alkenes, allenes, alkynes, and MBHADs. Chem. Commun.. 49(99):11588. http://dx.doi.org/10.1039/c3cc47368f
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