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Extra resources for Catalytic Asymmetric Friedel–Crafts Alkylations
2004) Angewandte Chemie, 116, 83–86; (2004) Angewandte Chemie – International Edition, 43, 84–87. M. L. (1996) Chemical Reviews, 96, 395–422; (b) Helmchen, G. and Pfaltz, A. M. L. (2003) Chemical Reviews, 103, 2921–2943. (a) Terada, M. and Sorimachi, K. -M. -L. (2007) Angewandte Chemie, 119, 5661–5663; (2007) Angewandte Chemie – International Edition, 46, 5565–5567. P. N. (2003) Science, 299, 1691–1693. Mulzer, J. (1999) Comprehensive Asymmetric Catalysis, Vol. N. Jacobsen, A. Pfaltz and H. Yamamoto), Springer, Berlin, pp.
Of practical importance, the catalyst system maintained the same catalytic activity even when the reaction was carried out in air. In subsequent investigations, a dramatic solvent effect was once again found in both reactivity and enantioselectivity . Thus, while the enantioselectivity was improved in alcoholic solvents such as iBuOH, weak coordinating solvents such as CCl4, toluene, CH2Cl2 or TTCE gave the product with the opposite conﬁguration. 1,1,2,2-Tetrachloroethane (TTCE) proved to be the best solvent for the production of the opposite enantiomer (ee up to 89%).
9), driven by the stacking interaction of the two phenyl groups of the ligand and nitroacrylate, leading to shielding of the Re-face. 15) . 9 Proposed transition state of the reaction. ). 01 mol mLÀ1. ) was added to the mixture. ) was added. After the reaction was complete (monitored by TLC), the reaction mixture was concentrated under reduced pressure at room temperature, and the residue was puriﬁed by ﬂash column chromatography on silica gel [eluted with CH2Cl2/petroleum ether (1/1, v/v) then pure CH2Cl2] to afford the desired product.