Journal of Organic Chemistry p. 963 - 972 (1988)
Update date:2022-09-26
Topics:
Wu, Pei-Lin
Chu, Min
Fowler, Frank W.
The 1-aza-Cope rearrangement of azavinylcyclohexene derivatives were investigated.It was observed that an N-acyl substituent on the 1-aza 1,5-diene provides a sufficient driving force for this normally contrathermodynamic process.Although simple derivatives have high activation energies proceeding in relative low overall yield, a methoxy substituent at C-4 of the aza diene as well as its incorporation into strained bicyclic ring systems facilitates the 1-aza-Cope rearrangement.Because the aza diene precursors are readily available by using the Diels-Alder reaction with acrolein derivatives, this process has synthetic potential for the preparation of nitrogen heterocycles.This scheme is illustrated with the preparation of a hydrolulolidine providing a formal total synthesis of (+/-)-aspidospermine.
View MoreContact:+86-579-85206992
Address:No 451 chouzhou north road ,room 1106 int'l business center , yiwu ,china
Changzhou naidechemical Co.Ltd
Contact:+86-519-82589807
Address:NO.25,Houyang street,Jintan,Changzhou City
Shangyu Sanhechemicals Co.,LTD.
Contact:86-0571-56696839
Address:Num.2952,Nanhuan Road,Binjiang District,Hangzhou,China
Ji'an Hairui Natural Plant Co. Ltd.
Contact:0796-8105528
Address:Meilin industry park, Qingyuan district Ji'an City, Jiangxi Province
HANGZHOU FOREWIN PHARMA CO., LTD
Contact:+86-571-89053961
Address:hangzhou
Doi:10.1016/j.tetlet.2008.12.087
(2009)Doi:10.1016/j.bmcl.2003.08.047
(2003)Doi:10.1080/00397910802138892
(2008)Doi:10.1021/jo800805w
(2008)Doi:10.1080/00397919408011508
(1994)Doi:10.1016/j.tet.2016.10.011
(2016)