Atropisomeric α-methyl substituted analogues of 4-(dimethylamino) pyridine: synthesis and evaluation as acyl transfer catalysts

…, A Maddaford, DP Leese, AJ Redgrave

Index: Spivey; Maddaford; Leese; Redgrave Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 15 p. 1785 - 1794

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Citation Number: 51

Abstract

The regioselectivity of α-metalation–methylation of N-BF3 adducts of 4-(dimethylamino) pyridines as a function of β-substitution is examined in attempts to prepare configurationally stable atropisomeric derivatives (I and II) having an α-methyl substituent and a β-biaryl stereogenic axis. The activity of some of these derivatives as catalysts for acyl transfer is examined and the kinetic resolution of 1-(1-naphthyl) ethanol catalysed by α-methyl chiral ...