Electronic Control of Chiral Quaternary Center Creation in the Intramolecular Asymmetric Heck Reaction
The Journal of Organic Chemistry2004Vol. 69(16), pp. 5187–5195
Citations Over TimeTop 15% of 2004 papers
Carl A. Busacca, Danja Grossbach, Scot Campbell, Yong Qiang Dong, Magnus Eriksson, Robert E. Harris, Paul‐James Jones, J. Kim, Jon C. Lorenz, Keith McKellop, Erin M. O’Brien, Fenghe Qiu, R. David Simpson, L. L. SMITH, Regina C. So, Earl Spinelli, Jana Vitous, Chiara Zavattaro
Abstract
The Boehringer-Ingelheim phosphinoimidazoline (BIPI) ligands were applied to the formation of chiral quaternary centers in the asymmetric Heck reaction. Several different substrates were examined in detail, using more than 70 members of this new ligand class. Hammett relationships were determined through systematic variation of the ligand electronics. All substrates showed essentially the same Hammett behavior, where enantioselectivity increased as the ligands were made more electron-deficient. Ligand optimization has led to catalysts which give the highest enantioselectivities reported to date for these difficult systems.
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