The role of achiral pyrazolidinone templates in enantioselective diels-alder reactions: Scope, limitations, and conformational insights

…, LM Stanley, X Nie, L Venkatraman, M Liu…

Index: Sibi, Mukund P.; Stanley, Levi M.; Nie, Xiaoping; Venkatraman, Lakshmanan; Liu, Mei; Jasperse, Craig P. Journal of the American Chemical Society, 2007 , vol. 129, # 2 p. 395 - 405

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Citation Number: 66

Abstract

We have evaluated the role of achiral pyrazolidinone templates in conjunction with chiral Lewis acids in room temperature, enantioselective Diels-Alder cycloadditions. The role of the fluxional N (1) substituent was examined, with the bulky 1-naphthylmethyl group providing enantioselectivities up to 99% ee, while templates with smaller fluxional groups gave lower selectivities. High selectivities were also observed in reactions of 7d with chiral ...