No abstract

The diastereoselective synthesis of anti -γ− oxo-αaminocarboxylates by aminoalkylation of ketones with in situ generated ternary iminium salts from inexpensive starting materials is described. These compounds are easily transformed diastereoselectively into syn,anti-or anti,anti − γ -hydroxy-α -aminocarboxylates by the use of different reducing agents. The configuration of the products has been determined by NMR. The aminoalkylation of enamines and imines is also reported.

Iminium salts generated in situ from ethyl glyoxylate, secondary amines and 1-H-benzotriazole are demonstrated to be excellent reagents for the regioselective mono-aminoalkylation of indoles, phenols, furans and pyrroles. This method provides a simple and straightforward "one-pot" reaction sequence to a variety of ethyl α-aryl-α-amino acid esters 5 and 8 in high yields.

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ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.