Affiliation:
1. Bio-Organic and Photochemistry Laboratory, Department of Pharmaceutical Sciences Guru Nanak Dev University Amritsar 143 005 Punjab India
2. Post-Graduate Department of Physics University of Jammu Jammu Tawi 180 006 India
3. Toxicology Division Forensic Science Laboratory Mohali 160 059 Punjab India
Abstract
AbstractRegio‐ and stereoselective 1,3‐dipolar cycloadditions of C‐(3‐pyridyl)‐N‐phenylnitrone (2) with variedly substituted dipolarophiles (3, 4) were carried out to obtain substituted pyridyl‐isoxazolidines (5–8). Reductive cleavage of pyridyl‐isoxazolidines (5–8) with ammonium formate, methanol−THF solvents, at ambient temperature, in the presence of Pd/C provided a facile route for the synthesis of β3‐and β2,3‐amino alcohols (9–12), with a substitution pattern having pronounced influence on torsional angles. The obtained compounds (9–12) are valuable scaffolds which can be utilized for peptidomimetics. Thus, the present methodology for reductive opening of isoxazolidine ring avoids the disadvantages of using expensive apparatus and hazards involved in the use of hydrogen gas. The preferential formation of amino‐alcohols in case of bicyclic isoxazolidines (8a–c), which precludes any recyclization is rationalized by DFT calculations.
Subject
Molecular Biology,Molecular Medicine,General Chemistry,Biochemistry,General Medicine,Bioengineering