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Constrained 1‐Phenylethyl Amine Analogues as Chiral Auxiliaries in Stereoselective trans ‐β‐Lactam Formation via Staudinger Cycloaddition
Author(s) -
Kurteva Vanya,
Alexandrova Maria
Publication year - 2019
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3471
Subject(s) - chemistry , ethylamine , cycloaddition , stereoselectivity , imine , enantiomer , lactam , amine gas treating , staudinger reaction , stereochemistry , medicinal chemistry , organic chemistry , catalysis
The efficiency of enantiomeric 1‐aminoindane and 1,2,3,4‐tetrahydro‐1‐naphthylamine as chiral auxiliaries in trans ‐ß‐lactam formation via Staudinger cycloaddition is examined. Aromatic aldehydes possessing one, two, or three methoxyl groups are used as imine precursors, and the influence of their number and position on the reaction output is studied. A comparison with the results obtained from 1‐phenylethyl and 1‐(2‐naphthyl)ethylamine‐derived imines is performed.