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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
Lewis acids
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:
It is part of: Organic Letters, 2014, vol. 16, num. 23, p. 6220-6223
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ISSN: 1523-7060
Appears in Collections:Articles publicats en revistes (Mineralogia, Petrologia i Geologia Aplicada)

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