.pi.-Allylpalladium Formation from Allylic Amines via N,N-Ditosylimides and N-Tosylamides: Efficient Synthesis of the Antiviral Agent Carbovir
摘要:
Allylic amines can be easily converted into their N,N-ditosylimides or N-tosylamides which are sufficiently good leaving groups to afford pi-allylpalladium complexes and, hence, with nucleophiles, new allylic systems with retention of configuration. The synthetic utility of this process has been demonstrated by an efficient synthesis of the antiviral agent (+/-)-carbovir,(1) from cyclopentadiene in only seven steps and 13% overall yield.
Transition-metal-controlled synthesis of (.+-.)-aristeromycin and (.+-.)-2',3'-diepi-aristeromycin. An unusual directive effect in hydroxylations
作者:Barry M. Trost、Gee Hong. Kuo、Torre. Benneche
DOI:10.1021/ja00210a064
日期:1988.1
Light/Palladium‐Promoted Benzylic C−H Acylation Using a Benzoyl Group as the Photo‐Directing Group
作者:Yusuke Masuda、Naoki Ishida、Masahiro Murakami
DOI:10.1002/asia.201801881
日期:2019.2
2‐Methylphenyl ketones undergo site‐selective acylation at the benzylic position when treated with acid anhydride under UV irradiation in the presence of a palladium catalyst. The benzoyl carbonyl group serves as the photo‐directinggroup so that the ortho benzylicC−H bond is activated site‐selectively.