e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521
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
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 ...
![7,9-dimethyl-4-oxa-7,9-diazabicyclo[3.2.2]nonane-6,8-dione Structure](https://image.chemsrc.com/caspic/378/85168-14-5.png)
![1,4-dimethyl-3-[2-((tert-butyldimethylsilyl)oxy)ethyl]-2,5-piperazinedione Structure](https://image.chemsrc.com/caspic/302/85168-16-7.png)
![1,4-dimethyl-3-[2-((tert-butyldimethylsilyl)oxy)ethyl]-6-(2-pyridylthio)-2,5-piperazinedione Structure](https://image.chemsrc.com/caspic/264/85168-17-8.png)