Synthesis and Stereochemical Characterization of a Novel Chiral α-Tetrazole Binaphthylazepine Organocatalyst

Year: 2022

Authors: Summa A., Scafato P., Belviso S., Monaco G., Zanasi R., Longhi G., Abbate S., Superchi S.

Autors Affiliation: Univ Basilicata, Dept Sci, Via Ateneo Lucano 10, I-85100 Potenza, Italy; Univ Salerno, Dept Chem & Biol A Zambelli, Via Giovanni Paolo 2, I-84084 Salerno, Italy; Univ Brescia, Dept Mol & Translat Med, Viale Europa 11, I-25123 Brescia, Italy; CSMT, Unit Brescia, CNR INO, I-25123 Brescia, Italy.

Abstract: A novel alpha-tetrazole-substituted 1,1 ’-binaphthylazepine chiral catalyst has been synthesized and its absolute configuration has been determined by DFT computational analysis of the vibrational circular dichroism (VCD) spectrum of its precursor. The VCD analysis, carried out through the model averaging method, allowed to assign the absolute configuration of a benzylic stereocenter in the presence of a chiral binaphthyl moiety. The 1,1 ’-binaphthylazepine tetrazole and the nitrile its immediate synthetic precursor, have been preliminarily tested as chiral organocatalysts in the asymmetric intramolecular oxa-Michael cyclization of 2-hydroxy chalcones for the synthesis of chiral flavanones obtaining low enantioselectivity.

Journal/Review: MOLECULES

Volume: 27 (16)      Pages from: 5113-1  to: 5113-14

More Information: This research was funded by Project PON RI 2014-2020 BIOFEEDSTOCK (ARS01_00985).
KeyWords: organocatalysis; binaphthylazepines; vibrational circular dichroism; flavanones; absolute configuration
DOI: 10.3390/molecules27165113

Citations: 2
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