161671-34-7Relevant articles and documents
Deprotection of N-tert-butoxycarbonyl (Boc) groups in the presence of tert-butyl esters
Lin,Lanza T.,De Laszlo,Truong,Kamenecka,Hagmann
, p. 7013 - 7016 (2000)
Deprotection of Boc groups in the presence of tert-butyl esters was achieved by using concentrated H2SO4 (1.5-3.0 equiv.) in tBuOAc or MeSO3H (1.5-3.0 equiv.) in tBuOAc:CH2Cl2 (4:1 v/v). The yields ranged from 70 to 100% for a variety of amino acid and dipeptide substrates. (C) 2000 Elsevier Science Ltd.
Asymmetric addition of Reformatsky-type reagent to imines utilizing diisopropyl tartrate as a chiral auxiliary
Ukaji, Yutaka,Takenaka, Shoichi,Horita, Yoshie,Inomata, Katsuhiko
, p. 254 - 255 (2001)
The asymmetric nucleophilic addition of Reformatsky-type reagent to imines, which were prepared from aldehydes and 2-aminophenols, was achieved by the use of diisopropyl (R,R)-tartrate as a chiral auxiliary to afford the corresponding β-amino acid ester derivatives with excellent enantioselectivities. In order to realize reproducible higher stereoselection, the addition of a small amount of water was crucial.
A chiral ligand mediated aza-conjugate addition strategy for the enantioselective synthesis of β-amino esters that contain hydrogenolytically sensitive functionality
Archer, Robert M.,Hutchby, Marc,Winn, Caroline L.,Fossey, John S.,Bull, Steven D.
, p. 8838 - 8847 (2015/10/20)
Aza-conjugate addition of the lithium anion of N-trimethylsilyl-p-methoxybenzylamine to tert-butyl enoate acceptors, in the presence of a stoichiometric amount of enantiopure 1,2-dimethoxy-1,2-diphenylethane and excess trimethylsilyl chloride, affords ter
Parallel synthesis of homochiral β-amino acids
Davies, Stephen G.,Mulvaney, Andrew W.,Russell, Angela J.,Smith, Andrew D.
, p. 1554 - 1566 (2008/02/09)
The parallel asymmetric synthesis of an array of 30 β-amino acids of high enantiomeric purity using the conjugate addition of homochiral lithium N-benzyl-N-(α-methylbenzyl)amide as the key step is accomplished. The experimental simplicity and highly practical nature of the protocol is demonstrated by the efficient parallel conversion of 15 α,β-unsaturated esters to both enantiomeric series of the corresponding β-amino acids in high overall yields and selectivities with minimal purification involved in each step of the reaction protocol.
