Features and Applications of [Rh (CO) 2Cl] 2-Catalyzed Alkylations of Unsymmetrical Allylic Substrates

BL Ashfeld, KA Miller, AJ Smith, K Tran…

Index: Ashfeld, Brandon L.; Miller, Kenneth A.; Smith, Anna J.; Tran, Kristy; Martin, Stephen F. Journal of Organic Chemistry, 2007 , vol. 72, # 24 p. 9018 - 9031

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Citation Number: 30

Abstract

A novel regio-and stereoselective [Rh (CO) 2Cl] 2-catalyzed allylic alkylation of unsymmetrical allylic carbonates was discovered. The regioselectivity of the reaction favors product ratios in which substitution occurs at the carbon bearing the leaving group. When an enantiomerically enriched carbonate (≥ 99% ee) was examined, the Rh (I)-catalyzed allylic alkylation proceeded stereoselectively to provide the alkylation product with retention of ...