A1 Journal article (refereed)
Stereoselective synthesis and transformation of pinane-based 2-amino-1,3-diols (2021)

Bajtel, Á., Raji, M., Haukka, M., Fülöp, F., & Szakonyi, Z. (2021). Stereoselective synthesis and transformation of pinane-based 2-amino-1,3-diols. Beilstein Journal of Organic Chemistry, 17, 983-990. https://doi.org/10.3762/bjoc.17.80

JYU authors or editors

Publication details

All authors or editors: Bajtel, Ákos; Raji, Mounir; Haukka, Matti; Fülöp, Ferenc; Szakonyi, Zsolt

Journal or series: Beilstein Journal of Organic Chemistry

ISSN: 2195-951X

eISSN: 1860-5397

Publication year: 2021

Publication date: 03/05/2021

Volume: 17

Pages range: 983-990

Publisher: Beilstein Institut

Publication country: Germany

Publication language: English

DOI: https://doi.org/10.3762/bjoc.17.80

Publication open access: Openly available

Publication channel open access: Open Access channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/75441

Abstract

A library of pinane-based 2-amino-1,3-diols was synthesised in a stereoselective manner. Isopinocarveol prepared from (−)-α-pinene was converted into condensed oxazolidin-2-one in two steps by carbamate formation followed by a stereoselective aminohydroxylation process. The relative stereochemistry of the pinane-fused oxazolidin-2-one was determined by 2D NMR and X-ray spectroscopic techniques. The regioisomeric spiro-oxazolidin-2-one was prepared in a similar way starting from the commercially available (1R)-(−)-myrtenol (10). The reduction or alkaline hydrolysis of the oxazolidines, followed by reductive alkylation resulted in primary and secondary 2-amino-1,3-diols, which underwent a regioselective ring closure with formaldehyde or benzaldehyde delivering pinane-condensed oxazolidines. During the preparation of 2-phenyliminooxazolidine, an interesting ring–ring tautomerism was observed in CDCl3.

Keywords: organic compounds; monoterpenes; tautomerism; chemical synthesis

Free keywords: 2-amino-1,2-diol; monoterpene; oxazolidin-2-one; stereoselective; tautomerism

Contributing organizations

Ministry reporting: Yes

Reporting Year: 2021

JUFO rating: 1