Please use this identifier to cite or link to this item:
http://hdl.handle.net/2445/169228
Title: | Substrate-controlled Michael additions of chiral ketones to enones |
Author: | Fàbregas, Mireia Gómez Palomino, Alejandro Pellicena Zanón, Miquel Reina, D.F. Romea, Pedro Urpí Tubella, Fèlix Font Bardia, Ma. Mercedes |
Keywords: | Àcids de Lewis Titani Cetones Lewis acids Titanium Ketones |
Issue Date: | 25-Nov-2014 |
Publisher: | American Chemical Society |
Abstract: | Substrate-controlled Michael additions of the titanium-(IV) enolate of lactate-derived ketone 1 to acyclic α,β-unsaturated ketones in the presence of a Lewis acid (TiCl4 or SnCl4) provide the corresponding 2,4-anti-4,5-anti dicarbonyl compounds in good yields and excellent diastereomeric ratios. Likely, the nucleophilic species involved in such additions are bimetallic enolates that may add to enones through cyclic transition states. Finally, further studies indicate that a structurally related β-benzyloxy chiral ketone can also participate in such stereocontrolled conjugate additions. |
Note: | Versió postprint del document publicat a: https://doi.org/10.1021/ol503133j |
It is part of: | Organic Letters, 2014, vol. 16, num. 23, p. 6220-6223 |
URI: | http://hdl.handle.net/2445/169228 |
Related resource: | https://doi.org/10.1021/ol503133j |
ISSN: | 1523-7060 |
Appears in Collections: | Articles publicats en revistes (Mineralogia, Petrologia i Geologia Aplicada) |
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