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2017-02-03

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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/106619

A Useful allene for the stereoselective synthesis of protected quaternary 2-amino-2-vinyl-1,3-diols

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https://doi.org/10.1021/acs.joc.6b02765

Abstract

Treatment of readily available allene 1 with Cy2BH followed by addition of an aldehyde led to quaternary protected 2-amino-2-vinyl-1,3-diols in high yield and excellent stereochemical purity. The choice of benzoyl as N-protecting group is critical since the observed N- to O-Bz transfer during the process prevents later undesired isomerizations in the adducts and keeps all heteroatoms protected.

Subject

Síntesi orgànica, Aldehids, Esfingolípids, Inhibidors enzimàtics

Subject (English)

Organic synthesis, Aldehydes, Sphingolipids, Enzyme inhibitors

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Articles publicats en revistes (Química Inorgànica i Orgànica)

Citation

RODRÍGUEZ RAMÍREZ, Aleix, et al. A Useful allene for the stereoselective synthesis of protected quaternary 2-amino-2-vinyl-1,3-diols. Journal of Organic Chemistry. 2017. Vol. 82, num. 3, pags. 1851-1855. ISSN 0022-3263. [consulted: 19 of August of 2026]. Available at: https://hdl.handle.net/2445/106619

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