Regioselective functionalization of bicyclic piperazinedione bridgehead carbanions

…, J Josey, R Armstrong, H Meyers

Index: Williams, Robert M.; Dung, Jen-Sen; Josey, John; Armstrong, Robert W.; Meyers, Harold Journal of the American Chemical Society, 1983 , vol. 105, # 10 p. 3214 - 3220

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Citation Number: 25

Abstract

Abstract: Generation of the bridgehead carbanions of bicyclic piperazinediones 2 and 3 with LDA in THF at-78 OC (kinetic conditions) followed by quenching with various electrophiles results in mixtures of the two monosubstitution products 12 and 13 with relatively poor regiochemical control. Addition of HMPA to 2 and 3 followed by LDA treatment and addition of an electrophile significantly favors functionalization of the carbanion adjacent to the ...