Divergent Method to <i>trans</i>-5-Hydroxy-6-alkynyl/alkenyl-2-piperidinones: Syntheses of (−)-Epiquinamide and (+)-Swainsonine
作者:Chang-Mei Si、Zhuo-Ya Mao、Han-Qing Dong、Zhen-Ting Du、Bang-Guo Wei、Guo-Qiang Lin
DOI:10.1021/acs.joc.5b00803
日期:2015.6.5
An efficient diastereoselective approach to access trans-5-hydroxy-6-alkynyl/alkenyl-2-piperidinones has been developed through nucleophilic addition of α-chiral aldimines using alkynyl/alkenyl Grignardreagents. The diastereoselectivity of alkenyl in C-6 position of 2-piperidinone was controlled by α-alkoxy substitution, while the alkynyl was controlled by the coordination of the α-alkoxy substitution
Synthesis of α-Substituted Allylic Amines via a Modified Bruylants Reaction
作者:Claude Agami、François Couty、Gwilherm Evano
DOI:10.1021/ol0059908
日期:2000.7.1
iminium ion promoter from alpha-amino nitriles, is an efficient additive in the Bruylants reaction involving vinylic Grignards. Improved yields of allylic amines were obtained when the starting alpha-amino nitrile was treated with this silver salt prior to its reaction with the vinylic Grignard. This improvement was not observed in the case of acetylenic Grignards. The reactivity of other vinyl organometallics
Remote control by protecting groups in the diastereoselective addition of acetylides to 2-(4-quinolyl)propanol
作者:Giuseppe Guanti、Sara Perrozzi、Renata Riva
DOI:10.1016/s0957-4166(98)00418-2
日期:1998.11
Differently O-protected 2-(4-quinolyl)propanols undergo, in the presence of chloroformate esters, a regio- and stereoselective addition of acetylides on the carbon alpha to nitrogen with moderate to good diastereoselectivity. The bulkiness of the OH protecting group, which has a 1,7 relationship with the newly created stereocentre, appears to be mainly responsible for this remote stereocontrol. (C) 1998 Elsevier Science Ltd. All rights reserved.