151133-00-5Relevant articles and documents
Enantioselective Synthesis of β-Amino Acids. 6. High 1,2-Stereoinduction in the Preparation of Enantiopure 2(R)-Hydroxy-3(R)-N-benzoylamino-3-phenylpropionic Acid (Like Stereoisomer of Taxol's Side Chain).
Escalante, Jaime,Juaristi, Eusebio
, p. 4397 - 4400 (1995)
The remarkably high 1,2-stereoinduction encountered in the hydroxylation of 1-benzoyl-3-methyl-6(S)-phenylperhydropyrimidin-4-one allows for the preparation of enantiopure N-benzoyl (2R,3R)-3-phenylisoserine, the like stereoisomer of taxol's C-13 side chain.
Rapid stereoselective syntheses of heteroarene-fused azacycles via diastereoselective conjugate addition of heteroaryl substituted lithium amidest
Davies, Stephen G.,Fletcher, Ai M.,Holder, Katherine E.,Roberts, Paul M.,Thomson, James E.,Zimmer, David
, p. 919 - 941 (2019/08/01)
Conjugate addition of heteroaryl substituted lithium amides to a range of α,β-unsaturated esters followed by in situ enolate oxidation with (-)-(camphorsulfonyl)oxaziridine gave the corresponding α-hydroxy-β-amino esters. Subsequent Friedel-Crafts type cy
Diastereoselective Radical Couplings Enable the Asymmetric Synthesis of anti-β-Amino-α-hydroxy Carboxylic Acid Derivatives
Hidasová, Denisa,Janák, Martin,Jahn, Emanuela,Císa?ová, Ivana,Jones, Peter G.,Jahn, Ullrich
supporting information, p. 5222 - 5230 (2018/10/20)
anti-β-Amino-α-(aminoxy) esters or amides are synthesized by merging polar asymmetric aza-Michael additions of lithium 1-phenylethylamides to α,β-unsaturated carboxylic acid derivatives and diastereoselective radical couplings with the persistent free rad
Solid phase synthesis of novel α/β-tetrapeptides, electrospray ionization mass spectrometric evaluation of their metal cation complexation behavior, and conformational analysis using density functional theory (DFT)
Bandala, Yamir,Avina, Judit,Gonzalez, Tania,Rivero, Ignacio A.,Juaristi, Eusebio
, p. 349 - 358 (2008/12/20)
Thirty-four novel α/β-tetrapeptides (1-34) have been prepared employing solid-phase and in-parallel synthetic protocols. α/β- Tetrapeptides 1-34 were prepared by a combination of three α-amino acid residues (alanine (Ala), phenylalanine (Phe), and isoleucine (Ile)) with one β-amino acid residue (β3-homophenylglycine). The corresponding complexes of several selected α/β-tetrapeptides with alkali, alkaline earth, and transition metals, [tP + M+], were evaluated using ion electrospray-ionization mass spectrometry (ESI-MS). According to the results from analysis of mixtures, we can conclude that the position of the β-amino acid is determinant in the affinity toward different metal cations. Computational modeling (DFT, B3LYP 6-311++G) provided useful information regarding the most likely coordination sites of the metal ions on the receptor α/β-tetrapeptide 12, HO2C-α- Phe-α-Phe-α-Ile-β3-hPhg-NH2, as well as the conformational changes induced by the metal upon [tP + M+] complex formation. Copyright
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.
Asymmetric three- and [2 + 1]-component conjugate addition reactions for the stereoselective synthesis of polysubstituted piperidinones
Davies, Stephen G.,Roberts, Paul M.,Smith, Andrew D.
, p. 1405 - 1415 (2008/02/10)
The efficiency and stereoselectivity of the conjugate addition of lithium (Z)- or (E)-β-amino ester enolates, generated by lithium amide conjugate addition to an α,β-unsaturated ester or deprotonation of a β-amino ester, respectively, to a range of α,β-unsaturated acceptors has been investigated. Deprotonation of a β-amino ester with LDA, followed by conjugate addition to a chiral α,β-unsaturated oxazolidinone gives high 2,3-anti selectivity (～90% d.e.), with hydrogenolysis and purification to homogeneity generating stereodefined trisubstituted piperidinones as single stereoisomers. Asymmetric three-component couplings of α,β-unsaturated esters and alkylidene malonates initiated by lithium amide conjugate addition proceeds with high levels of 2,3-anti stereoselectivity, with hydrogenolysis giving tetrasubstituted piperidinones. This journal is The Royal Society of Chemistry.
Asymmetric synthesis of α-mercapto-β-amino acid derivatives: application to the synthesis of polysubstituted thiomorpholines
Candela-Lena, Jose I.,Davies, Stephen G.,Roberts, Paul M.,Roux, Bruno,Russell, Angela J.,Sanchez-Fernandez, Elena M.,Smith, Andrew D.
, p. 1135 - 1145 (2007/10/03)
Tandem conjugate addition of homochiral lithium N-benzyl-N-(α-methyl-p-methoxybenzyl)amide to tert-butyl cinnamate and enolate trapping with TsStBu proceeds with high diastereoselectivity to give a homochiral anti-α-tert-butylthio-β-amino ester
Homochiral lithium amides for the asymmetric synthesis of β-amino acids
Davies, Stephen G.,Garrido, Narciso M.,Kruchinin, Dennis,Ichihara, Osamu,Kotchie, Luke J.,Price, Paul D.,Mortimer, Anne J. Price,Russell, Angela J.,Smith, Andrew D.
, p. 1793 - 1811 (2007/10/03)
Secondary homochiral lithium amides derived from α-methylbenzylamine undergo highly diastereoselective conjugate additions to a range of α,β-unsaturated esters. The corresponding β-amino acids are readily liberated by successive N-debenzylation and ester hydrolysis, furnishing (R)-β-amino butyric acid, (R)-β-amino pentanoic acid, (S)-β-leucine, (R)-β-amino octanoic acid, (S)-β-phenylalanine, (S)-β-tyrosine methyl ether, (S)-β-tyrosine hydrochloride and (S)-β-(2-methoxyphenyl)-β-amino propanoic acid in high yields and high ee. The application of this procedure to the synthesis of the natural products (R)-β-DOPA and (R)-β-lysine is demonstrated. The development of a simplified one-pot reaction protocol applicable to the multi-gram scale synthesis of homochiral β-amino esters is also delineated.
Double asymmetric induction as a mechanistic probe: Conjugate addition for the asymmetric synthesis of a pseudotripeptide
Davies, Stephen G.,Hermann, Gesine J.,Sweet, Miles J.,Smith, Andrew D.
, p. 1128 - 1129 (2007/10/03)
Double asymmetric induction as a mechanistic probe indicates that, for the conjugate addition of (R)- and (S)-lithium N-benzyl-N-α-methylbenzylamide to (S)-3′-phenylprop-2′-enoyl-4-benzyloxazolidinone, the reactive conformation of the N-acyl oxazolidinone is the anti-s-cis form, facilitating the asymmetric synthesis of a pseudotripeptide.
A novel synthesis of the macrocyclic spermidine alkaloid (+)-(S)-dihydroperiphylline
Sergeyev, Sergey A.,Hesse, Manfred
, p. 161 - 167 (2007/10/03)
A novel, short, and highly stereoselective synthesis of the macrocyclic spermidine alkaloid (+)-(S)-dihydroperiphylline (15) is described. The key synthetic steps were the stereoselective addition of the chiral amine 1 to the cinnamate 2 and cyclization o
