The first non-symmetrically substituted conjugates of bispidine with monoterpenoids and amino acids. Synthesis and application for catalysis of addition of diethylzinc to aldehydes

A series of bispidine conjugates bearing monoterpene moieties and either l -proline or l -phenylalanine residues was synthesized. The synthesized bispidines can catalyze asymmetric ethylation of benzaldehydes with diethylzinc. The highest enantioselectivity of the addition reaction ( ee 24%) was ach...

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Bibliographic Details
Published in:Russian chemical bulletin 2024-08, Vol.73 (8), p.2248-2260
Main Authors: Ponomarev, K. Yu, Mozhaitsev, E. S., Li-Zhulanov, N. S., Okhina, A. A., Nefedov, A. A., Rogachev, A. D., Suslov, E. V., Dalinger, A. I., Vatsadze, S. Z., Volcho, K. P., Salakhutdinov, N. F.
Format: Article
Language:English
Subjects:
Aldehydes
Amino acids
Chemical synthesis
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Conjugates
Enantiomers
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Inorganic Chemistry
Organic Chemistry
Phenylalanine
Proline
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Summary:A series of bispidine conjugates bearing monoterpene moieties and either l -proline or l -phenylalanine residues was synthesized. The synthesized bispidines can catalyze asymmetric ethylation of benzaldehydes with diethylzinc. The highest enantioselectivity of the addition reaction ( ee 24%) was achieved for bispidine with (–)-α-pinene and Boc- l -proline moieties.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-024-4346-z