Regio- and Enantioselective Intermolecular Hydroacylation: Substrate-Directed Addition of Salicylaldehydes to Homoallylic Sulfides

Regio- and Enantioselective Intermolecular Hydroacylation: Substrate-Directed Addition of Salicylaldehydes to Homoallylic Sulfides

We report a Rh-catalyzed, regio- and enantioselective intermolecular olefin hydroacylation under mild conditions. Hydroacylations between homoallylic sulfides, containing a substrate-bound directing group, and salicylaldehyde derivatives occur in the presence of a spiro-phosphoramidite ligand, (R)-S...

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Veröffentlicht in:Journal of the American Chemical Society 2010-11, Vol.132 (46), p.16330-16333
Hauptverfasser: Coulter, Matthew M, Kou, Kevin G. M, Galligan, Baye, Dong, Vy M
Format: Artikel
Sprache:eng
Schlagworte:
Acylation
Aldehydes - chemistry
Allyl Compounds - chemistry
Ketones - chemical synthesis
Ketones - chemistry
Molecular Structure
Stereoisomerism
Sulfides - chemistry
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Zusammenfassung:We report a Rh-catalyzed, regio- and enantioselective intermolecular olefin hydroacylation under mild conditions. Hydroacylations between homoallylic sulfides, containing a substrate-bound directing group, and salicylaldehyde derivatives occur in the presence of a spiro-phosphoramidite ligand, (R)-SIPHOS-PE, to give α-branched ketones in >20:1 selectivity and up to 97% ee. Our conditions are also applicable to the asymmetric intermolecular hydroacylation of 1,2-disubstituted olefins.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja107198e