Enantiospecific and diastereoselective synthesis of anti α-hydrazino- and α-amino-β-hydroxyacids through “electrophilic amination” of β-hydroxyesters

Chemistry of Hydrazinoalcohols and their Heterocyclic Derivatives. Part 1. Synthesis of Hydrazinoalcohols

“…The first studies on the electrophilic amination of β-hydroxyesters were made by the research groups of Guanti and Genet [88][89][90][91]. They observed that β-hydroxyester enolates react smoothly with diazene dicarboxylates to give a readily separable mixture of syn (or threo) and anti (or erythro) adducts, in which the anti isomer is the main product.…”

“…The resulting anti isomers of N 1 ,N 2 -diprotected α-hydrazino-β-hydroxyesters, containing both hydrazinoalcohol and hydrazinoester moieties, proved to be useful starting materials for the preparation of various important compounds, e.g. aminosugar derivatives [94,95], β-lactam antibiotics [96,97], α-amino-β-hydroxyacids or esters [88,[98][99][100][101][102].…”

Methods for the Chemical Synthesis of Noncoded α‐Amino Acids found in Natural Product Peptides

“…In addition, b-hydroxy-a-amino acids are used as chiral building blocks in preparing precursors to important molecules [132][133][134][135][136][137]. Currently, various synthetic methods have been developed to prepare b-hydroxy-a- amino acids stereoselectively, which include asymmetric aldol reaction [138][139][140][141][142][143][144][145][146][147][148][149][150][151][152][153][154][155][156], alkylation [153][154][155][156], electrophilic amination and allylic amination [157,158], conjugate addition [159], cyanation [160], enantioselective hydrogenation [161], selective hydrolysis [135], rearrangement [162][163][164][165], regioselective aziridine ring opening [135,[166][167][168], dynamic kinetic resolution (DKR) [169][170]…”

Synthesis of alkylcarbazole aminoderivatives

“…Since then this method of amination has evolved and currently has different forms as well as different applications [3][4][5][6][7]. In this paper, the direct amination method relies on electrophilic substitution of the onium ion (NH=N + =NH or N≡N + NH 2 ), which is a protonated form of hydrazoic acid.…”