60448-81-9Relevant articles and documents
Hydrogen-Borrowing Alkylation of 1,2-Amino Alcohols in the Synthesis of Enantioenriched γ-Aminobutyric Acids
Hall, Christopher J. J.,Goundry, William R. F.,Donohoe, Timothy J.
supporting information, p. 6981 - 6985 (2021/03/01)
For the first time we have been able to employ enantiopure 1,2-amino alcohols derived from abundant amino acids in C?C bond-forming hydrogen-borrowing alkylation reactions. These reactions are facilitated by the use of the aryl ketone Ph*COMe. Racemisation of the amine stereocentre during alkylation can be prevented by the use of sub-stoichiometric base and protection of the nitrogen with a sterically hindered triphenylmethane (trityl) or benzyl group. The Ph* and trityl groups are readily cleaved in one pot to give γ-aminobutyric acid (GABA) products as their HCl salts without further purification. Both steps may be performed in sequence without isolation of the hydrogen-borrowing intermediate, removing the need for column chromatography.
Parallel kinetic resolution of acyclic γ-amino-α,β- unsaturated esters: Application to the asymmetric synthesis of 4-aminopyrrolidin-2-ones
Davies, Stephen G.,Lee, James A.,Roberts, Paul M.,Thomson, James E.,Yin, Jingda
supporting information; experimental part, p. 218 - 221 (2012/03/08)
Conjugate addition of a 50:50 pseudoenantiomeric mixture of lithium (R)-N-benzyl-N-(α-methylbenzyl)amide and lithium (S)-N-3,4- dimethoxybenzyl-N-(α-methylbenzyl)amide to a range of racemic acyclic γ-amino-α,β-unsaturated esters (derived from the corresponding α-amino acids) effects their efficient parallel kinetic resolution, allowing the preparation of enantiopure β,γ-diamino esters. The β,γ-diamino ester products of these reactions are readily converted into the corresponding substituted 4-aminopyrrolidin-2-ones via N-debenzylation and cyclization.
Reaction of 1-(R-sulfonyl)indoles with N,N-dibenzyl-β-amino alcohols
Kurkin,Karchava,Yurovskaya
, p. 1141 - 1148 (2007/10/03)
The reaction of 1-(methylsulfonyl)- and 1-(phenylsulfonyl)indoles with N,N-dibenzylamino alcohols leads to the formation of a mixture of isomeric 1-(β-aminoethyl)indoles.
