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2023-01-26

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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/196206

Protected syn-aldol compounds from direct, catalytic, and enantioselective reactions of N-acyl-1,3-oxazinane-2-thiones with aromatic acetals

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https://doi.org/10.1021/acs.orglett.2c04254

Abstract

A direct and asymmetric syn-aldol reaction of N-acyl-1,3-oxazinane-2-thiones with dialkyl acetals from aromatic acetals in the presence of 2-5 mol % [DTBM-SEGPHOS]NiCl2, TMSOTf, and lutidine has been developed. It has been established that the oxazinanethione heterocycle, used for the first time as a scaffold in asymmetric carbon-carbon bond-forming reactions, can be smoothly removed to give access to a variety of enantiomerically pure compounds with high synthetic value.

Subject

Aldehids, Estructura molecular

Subject (English)

Aldehydes, Molecular structure

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Articles publicats en revistes (Química Inorgànica i Orgànica)

Citation

MELLADO HIDALGO, Miguel, et al. Protected syn-aldol compounds from direct, catalytic, and enantioselective reactions of N-acyl-1,3-oxazinane-2-thiones with aromatic acetals. Organic Letters. 2023. Vol. 23, num. 4, pags. 659-664. ISSN 1523-7060. [consulted: 12 of August of 2026]. Available at: https://hdl.handle.net/2445/196206

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