Phosphoramidite-Rhodium Complexes as Catalysts for the Asymmetric [2+2+2] Cycloaddition of Alkenyl Isocyanates and Alkynes.

Pure and Applied Chemistry. Chimie Pure Et Appliquée
Rebecca Keller FriedmanTomislav Rovis

Abstract

The discovery and development of the asymmetric rhodium-catalyzed [2+2+2] cycloaddition of alkenyl isocyanates and exogenous alkynes to form indolizinone and quinolizinone scaffolds is described. This methodology has been expanded to include substituted alkenes and dienes, a variety of sterically and electronically diverse alkynes, and carbodiimides in place of the isocyanate. Through X-ray analysis of Rh(cod)/phosphoramidite complexes, additives that modify the enantio-determining step, and other experimental data, a mechanism has been proposed that explains lactam, vinylogous amide, and pyridone products and the factors governing their formation. Finally, we have applied this methodology to the synthesis of (+)-lasubine-II and (-)-209D.

References

Sep 16, 2004·Journal of the American Chemical Society·Hung A DuongJanis Louie
Mar 2, 2006·Journal of the American Chemical Society·Robert T Yu, Tomislav Rovis
Feb 21, 2009·Angewandte Chemie·Brandon R Galan, Tomislav Rovis
Jul 3, 2009·Journal of the American Chemical Society·Rebecca Keller Friedman, Tomislav Rovis

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Citations

May 21, 2016·Organic & Biomolecular Chemistry·James D Neuhaus, Michael C Willis
Oct 12, 2011·Chemical Communications : Chem Comm·Todd K Hyster, Tomislav Rovis
Feb 27, 2013·The Journal of Organic Chemistry·Koichi MitsudoSeiji Suga
Jan 13, 2015·Journal of the American Chemical Society·Wen-Zhen ZhangTomislav Rovis
Nov 23, 2012·Organic Letters·Andrew T BrusoeErik J Alexanian
Mar 16, 2011·Journal of the American Chemical Society·Kevin M Oberg, Tomislav Rovis

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