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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.

Authors+Show Affiliations

Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.No affiliation info availableNo affiliation info availableNo affiliation info available

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_ L2 - https://doi.org/10.1021/ja107198e DB - PRIME DP - Unbound Medicine ER -