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Regio- and enantioselective intermolecular hydroacylation: substrate-directed addition of salicylaldehydes to homoallylic sulfides.
J Am Chem Soc. 2010 Nov 24; 132(46):16330-3.JA

Abstract

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.

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Authors+Show Affiliations

Coulter MM
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.
Kou KG
No affiliation info available
Galligan B
No affiliation info available
Dong VM
No affiliation info available

MeSH

AcylationAldehydesAllyl CompoundsKetonesMolecular StructureStereoisomerismSulfides

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21033718

Citation

Coulter, Matthew M., et al. "Regio- and Enantioselective Intermolecular Hydroacylation: Substrate-directed Addition of Salicylaldehydes to Homoallylic Sulfides." Journal of the American Chemical Society, vol. 132, no. 46, 2010, pp. 16330-3.
Coulter MM, Kou KG, Galligan B, et al. Regio- and enantioselective intermolecular hydroacylation: substrate-directed addition of salicylaldehydes to homoallylic sulfides. J Am Chem Soc. 2010;132(46):16330-3.
Coulter, M. M., Kou, K. G., Galligan, B., & Dong, V. M. (2010). Regio- and enantioselective intermolecular hydroacylation: substrate-directed addition of salicylaldehydes to homoallylic sulfides. Journal of the American Chemical Society, 132(46), 16330-3. https://doi.org/10.1021/ja107198e
Coulter MM, et al. Regio- and Enantioselective Intermolecular Hydroacylation: Substrate-directed Addition of Salicylaldehydes to Homoallylic Sulfides. J Am Chem Soc. 2010 Nov 24;132(46):16330-3. PubMed PMID: 21033718.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Regio- and enantioselective intermolecular hydroacylation: substrate-directed addition of salicylaldehydes to homoallylic sulfides. AU - Coulter,Matthew M, AU - Kou,Kevin G M, AU - Galligan,Baye, AU - Dong,Vy M, Y1 - 2010/10/29/ PY - 2010/11/2/entrez PY - 2010/11/3/pubmed PY - 2011/3/9/medline SP - 16330 EP - 3 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 132 IS - 46 N2 - 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. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/21033718/Regio__and_enantioselective_intermolecular_hydroacylation:_substrate_directed_addition_of_salicylaldehydes_to_homoallylic_sulfides_ DB - PRIME DP - Unbound Medicine ER -