Enantiodiscrimination of racemic electrophiles by diketopiperazine enolates: asymmetric synthesis of methyl 2-amino-3-aryl-butanoates and 3-methyl-aspartates
Enolates of (S)-N,N′-bis-(p-methoxybenzyl)-3-iso-propylpiperazine-2,5-dione exhibit high levels of enantiodiscrimination in alkylations with (RS)-1-aryl-1-bromoethanes and (RS)-2-bromoesters, affording substituted diketopiperazines containing two new stereogenic centres in high de. Deprotection and hydrolysis of the resultant substituted diketopiperazines provides a route to the asymmetric synthesis of homochiral methyl 2-amino-3-aryl-butanoates and 3-methyl-aspartates in high de and ee.
Bull, Steven D.,Davies, Stephen G.,Epstein, Simon W.,Garner, A. Christopher,Mujtaba, Nadeam,Roberts, Paul M.,Savory, Edward D.,Smith, Andrew D.,Tamayo, Juan A.,Watkin, David J.
p. 7911 - 7925
(2007/10/03)
The asymmetric synthesis of (2R,3R)- and (2R,3S)-3-methyl-aspartates via an enantiodiscrimination strategy
The enolate of (S)-N,N′-bis-(p-methoxybenzyl)-3-isopropylpiperazine-2,5-dione exhibits high levels of enantiodiscrimination towards racemic 2-bromo-propionate esters to afford adducts containing two new stereogenic centres which may be deprotected to affo
Bull,Davies,Garner,Mujtaba
p. 781 - 784
(2007/10/03)
More Articles about upstream products of 354118-71-1