169534-80-9Relevant academic research and scientific papers
O-(α-Phenylethyl)hydroxylamine as a ‘chiral ammonia equivalent’: synthesis and resolution of 5-oxopyrrolidine- and 6-oxopiperidine-3-carboxylic acids
Kleban, Ihor,Tymtsunik, Andriy V.,Rassukana, Yuliya V.,Grygorenko, Oleksandr O.
, p. 1817 - 1822 (2017)
An approach to the synthesis and resolution of five- and six-membered lactams (i.e., 5-oxopyrrolidine- and 6-oxopiperidine-3-carboxylic acids) is described. The method relies on the one-pot Michael reaction—cyclization of itaconic acid or diethyl homoitaconate and enantiopure O-(α-phenylethyl)hydroxylamine as a ‘chiral ammonia equivalent’. It is shown that this chiral auxiliary can be used for the separation of diastereomeric lactam products and then easily removed by catalytic hydrogenolysis.
Chiral Oximes in Asymmetric Synthesis. Addition of Organometallic Reagents to O-(1-Phenylethyl) Aldoximes
Brown, David S.,Gallagher, Peter T.,Lightfoot, Andrew P.,Moody, Christopher J.,Slawin, Alexandra M. Z.,Swann, Elizabeth
, p. 11473 - 11488 (2007/10/02)
Addition of Grignard and organolithium reagents to O-(1-phenylethyl) aldoximes in the presence of boron trifluoride etherate gives secondary hydroxylamines in 21-84percent yield with up to 95percent diastereomeric excess.
