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Asymmetric synthesis of aminocyclooctenecarbonitriles: Cyclooctene β-lactam and hydroxyaminocyclooctene carboxylic precursors

Author:
Aydin, Busra Ozturk, Yurtoglu, Emine, Arcelik, Nejat, Sahin, Ertan, Secen, Hasan, Altundas, Ramazan
Source:
Tetrahedron letters 2019 v.60 no.3 pp. 284-287
ISSN:
0040-4039
Subject:
acid hydrolysis, amino acids, beta-lactams, crystallization, enantiomers, ethyleneimine, moieties
Abstract:
Enantiopure β-aminocyclooctenenitriles, as precursors of β-amino acids and β-lactams, were synthesized from a readily available chloroalkene nitrile and (S)-methylbenzylamine via a straightforward substitution reaction and purified by crystallization. Acidic hydrolysis of the nitrile groups to their corresponding amides followed by DCC assisted carbonyl group activation gave novel α,β-unsaturated lactams. The treatment of 3-bromo-8-chlorocyclooctenecarbonitrile with (S)-methylbenzylamine furnished a diastereomeric mixture of bromoaminocyclooctenecarbonitriles via an SN2′ pathway rather than bromide substitution via an SN2 pathway. The diastereomeric mixture of bromoaminocyclooctanecarbonitriles provided two novel aziridines upon heating. TFA catalyzed aziridine ring opening gave γ-hydroxyl-β-aminocyclooctenecarbonitriles and γ-amino-β-hydroxycyclooctenecarbonitriles.
Agid:
6264365