Convenient Synthesis oftrans-β-Amino Carboxylic Esters with an Azetidine Skeleton via Rearrangement of β,γ-Aziridino α-amino Esters
- 19 September 2007
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (21) , 4399-4402
- https://doi.org/10.1021/ol7020466
Abstract
A short and facile approach to biologically interesting N-protected alkyl 3-aminoazetidine-2-carboxylic esters, a new class of conformationally restricted β-amino esters, was developed. Reduction of anti-β,γ-aziridino-α-(N-diphenylmethylidene)amino esters and subsequent regioselective intramolecular ring opening of the β,γ-aziridine ring via nucleophilic attack of the α-amino function afforded the trans-azetidines.Keywords
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