154129-74-5Relevant academic research and scientific papers
2-Thiazolyl α-amino ketones: A new class of reactive intermediates for the stereocontrolled synthesis of unusual amino acids
Dondoni,Perrone
, p. 1162 - 1176 (1993)
The thiazole-based one carbon homologation of four α-amino acids (L-phenylalanine, L-leucine, L-threonine, and L-serine) to the corresponding α-hydroxy β-amino aldehydes and acids in both configurations at C(α), is described. The methodology involves the following key operations: (i) the conversion of an α-amino ester to a 2-thiazolyl α-amino ketone; (ii) the stereocontrolled reduction of a ketone carbonyl to either syn or anti α,β-amino alcohols; (iii) the aldehyde release from the thiazole ring; (iv) the oxidation of the aldehyde to a carboxylic acid. The methodology was only partially applied to L-phenylglycine because of some limitations in operation (i).
Memory of Chirality Concept in Asymmetric Intermolecular Michael Addition of α-Amino Ester Enolates to Enones and Nitroalkenes
Veeraswamy, Vadlamuri,Goswami, Gaurav,Mukherjee, Satobhisha,Ghosh, Koena,Saha, Manik Lal,Sengupta, Arunava,Ghorai, Manas K.
, p. 1106 - 1115 (2018/02/09)
A highly stereoselective asymmetric intermolecular conjugate addition of α-amino ester derivatives to cyclic enones via the memory of chirality (MOC) concept in high yields with excellent diastereo- and enantioselectivity (dr >99:1, up to 99% ee) is reported. The applicability and the generality of the strategy was demonstrated by its further exploration to acyclic α,β-unsaturated ketone and aromatic nitroalkenes, resulting in the formation of δ-keto-α-amino ester derivative and γ-nitro-α-amino ester derivatives, respectively, with excellent ee and dr.
Oxazolidinones and 2,5-Dihydrofurans via Zinc-Catalyzed Regioselective Allenylation Reactions of l -α-Amino Aldehydes
Zamani, Farzad,Pyne, Stephen G.,Hyland, Christopher J. T.
, p. 6819 - 6830 (2017/07/17)
The simultaneous control of diastereoselectivity and regioselectivity in Zn-catalyzed allenylation reactions of N-protected l-α-amino aldehydes is reported. A reversal in diastereoselectivity could be realized by variation of the α-amino aldehyde protecti
