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2016-02

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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/98971

A general method for the synthesis of enantiopure 1,5-amino alcohols

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http://dx.doi.org/10.1002/ejoc.201501409

Abstract

A variety of (R)-phenylglycinol-derived oxazolopiperidone lactams 1-14 were converted to linear-chain enantiopure amino diols 15-26 by reduction with LiNH2BH3 in an unprecedented process involving the simultaneous reductive opening of the oxazolidine and lactam rings. Subsequent removal of the phenylethanol moiety gave enantiopure 5-amino-1-pentanols bearing substituents at the 2-, 3-, 4-, 2,2-, 2,3- 2,4- and 3,4-positions (28-36), which were isolated as their N-Boc derivatives.

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Síntesi orgànica, Síntesi asimètrica, Reducció química, Lactames

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Organic synthesis, Asymmetric synthesis, Reduction (Chemistry), Lactams

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Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
Articles publicats en revistes (Institut de Biomedicina (IBUB))

Citation

GUIGNARD, Guillaume Michel Pablo, et al. A general method for the synthesis of enantiopure 1,5-amino alcohols. European Journal of Organic Chemistry. 2016. Vol. 2016, num. 4, pags. 693-703. ISSN 1434-193X. [consulted: 6 of June of 2026]. Available at: https://hdl.handle.net/2445/98971

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