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Kwon Group – Professor Product Portal

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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 Sigma–Aldrich. 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
Link to Aldrichimica Acta review (2016)

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For recent articles from the Kwon Laboratory:

Products available at Aldrich from the Kwon Laboratory

     

Henry CE, Xu Q, Fan YC, Martin TJ, Belding L, Dudding T, Kwon O.
J Am Chem Soc. 2014 Aug 14
The routine application of C(sp3)-hybridized nucleophiles in cross-coupling reactions remains an unsolved challenge in organic chemistry. The sluggish transmetalation rates observed for the preferred organoboron reagents in such transformations are a consequence of the two-electron mechanism underlying the standard catalytic approach...Read More
Ian P Andrews, Ohyun Kwon
Chemical science (Royal Society of Chemistry : 2010) 2012-01-01
In this study we performed the total synthesis of the terpene indole alkaloid (+)-ibophyllidine through a pathway involving asymmetric phosphine catalysis, with our novel l-4-hydroxyproline-derived chiral phosphine mediating the key [3 + 2] annulation...Read More
Yi Chiao Fan, Ohyun Kwon
Chemical Communications 2013-12-25
In nucleophilic phosphine catalysis, tertiary phosphines undergo conjugate additions to activated carbon-carbon multiple bonds to form β-phosphonium enolates, β-phosphonium dienolates, β-phosphonium enoates, and vinyl phosphonium ylides as intermediates...Read More