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Conformational analysis of 3‐ketopiperidines. Vicinal N 1 C (2) ‐alkyl interactions
Author(s) -
Katvalyan H. T.,
Shashkov A. S.,
Mistryukov E. A.
Publication year - 1985
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.5570220114
Subject(s) - chemistry , vicinal , substituent , diastereomer , alkyl , nitrogen , chemical shift , stereochemistry , computational chemistry , crystallography , medicinal chemistry , organic chemistry
Chemical equilibration and 1 H‐nmr spectroscopic studies on 1,2,5‐substituted 3‐ketopiperidines have been carried out. With the bulky t ‐butyl group on nitrogen the C (2) ‐methyl substituent is highly favored in the axial configuration. This phenomenon constitutes the basis of an efficient method of controlling diastereomer stabilities by varying the nitrogen substituent in the 3‐keto‐ and 4‐ketopiperidine series.