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O-substituted alkyl aldehydes for rhodium-catalyzed intermolecular alkyne hydroacylation: the utility of methylthiomethyl ethers.
Org Lett. 2011 Mar 04; 13(5):998-1000.OL

Abstract

Combining α-methylthiomethyl (MTM) ether substituted aldehydes and 1-alkynes in the presence of [Rh(dppe)]ClO(4) results in efficient intermolecular alkyne hydroacylation to deliver α-O-MTM-substituted enone products. The product MTM ethers can be converted to the free hydroxyl group either in situ, by the addition of water to the completed reaction, or in a separate operation, by the action of silver nitrate.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Parsons SR
Department of Chemistry, University of Oxford, Oxford, UK.
Hooper JF
No affiliation info available
Willis MC
No affiliation info available

MeSH

AldehydesAlkynesCatalysisCombinatorial Chemistry TechniquesEthersKetonesMolecular StructureRhodiumSilver NitrateWater

Pub Type(s)

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

Language

eng

PubMed ID

21309521

Citation

Parsons, Scott R., et al. "O-substituted Alkyl Aldehydes for Rhodium-catalyzed Intermolecular Alkyne Hydroacylation: the Utility of Methylthiomethyl Ethers." Organic Letters, vol. 13, no. 5, 2011, pp. 998-1000.
Parsons SR, Hooper JF, Willis MC. O-substituted alkyl aldehydes for rhodium-catalyzed intermolecular alkyne hydroacylation: the utility of methylthiomethyl ethers. Org Lett. 2011;13(5):998-1000.
Parsons, S. R., Hooper, J. F., & Willis, M. C. (2011). O-substituted alkyl aldehydes for rhodium-catalyzed intermolecular alkyne hydroacylation: the utility of methylthiomethyl ethers. Organic Letters, 13(5), 998-1000. https://doi.org/10.1021/ol1030662
Parsons SR, Hooper JF, Willis MC. O-substituted Alkyl Aldehydes for Rhodium-catalyzed Intermolecular Alkyne Hydroacylation: the Utility of Methylthiomethyl Ethers. Org Lett. 2011 Mar 4;13(5):998-1000. PubMed PMID: 21309521.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - O-substituted alkyl aldehydes for rhodium-catalyzed intermolecular alkyne hydroacylation: the utility of methylthiomethyl ethers. AU - Parsons,Scott R, AU - Hooper,Joel F, AU - Willis,Michael C, Y1 - 2011/02/10/ PY - 2011/2/12/entrez PY - 2011/2/12/pubmed PY - 2011/5/7/medline SP - 998 EP - 1000 JF - Organic letters JO - Org Lett VL - 13 IS - 5 N2 - Combining α-methylthiomethyl (MTM) ether substituted aldehydes and 1-alkynes in the presence of [Rh(dppe)]ClO(4) results in efficient intermolecular alkyne hydroacylation to deliver α-O-MTM-substituted enone products. The product MTM ethers can be converted to the free hydroxyl group either in situ, by the addition of water to the completed reaction, or in a separate operation, by the action of silver nitrate. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/21309521/O_substituted_alkyl_aldehydes_for_rhodium_catalyzed_intermolecular_alkyne_hydroacylation:_the_utility_of_methylthiomethyl_ethers_ L2 - https://doi.org/10.1021/ol1030662 DB - PRIME DP - Unbound Medicine ER -