219916-58-2Relevant academic research and scientific papers
Conjugate additions of organocuprates to a 3-methylene-6-isopropyldiketopiperazine acceptor for the asymmetric synthesis of homochiral α-amino acids
Bull,Davies,Garner,O'Shea
, p. 3281 - 3287 (2007/10/03)
Addition of a range of organocuprates to (S)-N,N′-bis(p-methoxybenzyl)-3-methylene-6-isopropylpiperazine-2, 5-dione 8 affords cis-3-isopropyl-6-alkyldiketopiperazines in excellent yield and >95% de. Subsequent deprotection and hydrolysis of these cis-3-isopropyl-6-alkyldiketopiperazines affords homochiral (S)-α-amino acids in excellent yield.
A chiral relay auxiliary for the synthesis of homochiral α-amino acids
Bull, Steven D.,Davies, Stephen G.,Epstein, Simon W.,Leech, Michael A.,Ouzman, Jacqueline V. A.
, p. 2321 - 2330 (2007/10/03)
A new chiral auxiliary (3S)-N,N′-bis(p-methoxybenzyl)-3-isopropylpiperazine-2,5-dione 7 has been developed for the asymmetric synthesis of α-amino acids. The auxiliary 7 employs a novel chiral relay network based on non-stereogenic N-benzyl protecting groups which enhance the diastereoselectivity observed during alkylation of its C6 enolate 25.
Chiral relay auxiliary for the synthesis of enantiomerically pure α-amino acids
Bull, Steven D.,Davies, Stephen G.,Epstein, Simon W.,Ouzman, Jacqueline V. A.
, p. 659 - 660 (2007/10/03)
Chiral auxiliary (3S)-N,N′-bis(p-methoxybenzyl)-3-iso-propylpiperazine-2,5-dione employs a chiral relay network based on non-stereogenic N-benzyl protecting groups to enhance diastereocontrol during enolate alkylation.
Stereoselective conjugate addition of organocuprates to a dehydroalanine derived diketopiperazine
Bull, Steven D.,Davies, Stephen G.,O'Shea, Michael D.
, p. 3657 - 3658 (2007/10/03)
An asymmetric synthesis of homochiral α-amino acids has been developed which is based on the conjugate addition of organocuprates to the dehydroalanine equivalent (3S)-N,N′-bis(p-methoxybenzyl)-3-isopropyl-6-methylenepiperazine-2,5-dione 6.
