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Chiral Phosphoramide-Catalyzed Enantioselective Addition of Allylic Trichlorosilanes to Aldehydes. Preparative Studies with Bidentate Phosphorus-Based Amides

Scott E. Denmark,* Jiping Fu and Michael J. Lawler

*Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, Email:

S. E. Denmark, J. Fu, M. J. Lawler, J. Org. Chem., 2006, 71, 1523-1536.

DOI: 10.1021/jo052203h

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A bidentate chiral phosphoramide based on a 2,2'-bispyrrolidine skeleton afforded good yield, efficient turnover, and high enantioselectivity in allylation reactions of various unsaturated aldehydes with substituted allylic trichlorosilanes. The reaction of γ-disubstituted allylic trichlorosilanes allowed the construction of stereogenic, quaternary centers.

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Key Words

Allylic Alcohols, Organocatalysis

ID: J42-Y2006-370