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N-triflylthiophosphoramide catalyzed enantioselective Mukaiyama aldol reaction of aldehydes with silyl enol ethers of ketones.
Org Lett. 2010 Jun 04; 12(11):2476-9.OL

Abstract

The first Brønsted acid catalyzed asymmetric Mukaiyama aldol reaction of aldehydes using silyl enol ethers of ketones as nucleophiles has been reported. A variety of aldehydes and silyl enol ethers of ketones afforded the aldol products in excellent yields and good to excellent enantioselectivities. Mechanistic studies revealed that the actual catalyst may be changed from the silylated Brønsted acid to the Brønsted acid itself depending on the reaction temperature.

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Authors+Show Affiliations

Cheon CH
Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60615, USA.
Yamamoto H
No affiliation info available

MeSH

AldehydesCatalysisCombinatorial Chemistry TechniquesEthersKetonesMolecular StructureOrganothiophosphorus CompoundsSilanesStereoisomerismTemperature

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural

Language

eng

PubMed ID

20465277

Citation

Cheon, Cheol Hong, and Hisashi Yamamoto. "N-triflylthiophosphoramide Catalyzed Enantioselective Mukaiyama Aldol Reaction of Aldehydes With Silyl Enol Ethers of Ketones." Organic Letters, vol. 12, no. 11, 2010, pp. 2476-9.
Cheon CH, Yamamoto H. N-triflylthiophosphoramide catalyzed enantioselective Mukaiyama aldol reaction of aldehydes with silyl enol ethers of ketones. Org Lett. 2010;12(11):2476-9.
Cheon, C. H., & Yamamoto, H. (2010). N-triflylthiophosphoramide catalyzed enantioselective Mukaiyama aldol reaction of aldehydes with silyl enol ethers of ketones. Organic Letters, 12(11), 2476-9. https://doi.org/10.1021/ol100233t
Cheon CH, Yamamoto H. N-triflylthiophosphoramide Catalyzed Enantioselective Mukaiyama Aldol Reaction of Aldehydes With Silyl Enol Ethers of Ketones. Org Lett. 2010 Jun 4;12(11):2476-9. PubMed PMID: 20465277.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - N-triflylthiophosphoramide catalyzed enantioselective Mukaiyama aldol reaction of aldehydes with silyl enol ethers of ketones. AU - Cheon,Cheol Hong, AU - Yamamoto,Hisashi, PY - 2010/5/15/entrez PY - 2010/5/15/pubmed PY - 2010/8/18/medline SP - 2476 EP - 9 JF - Organic letters JO - Org Lett VL - 12 IS - 11 N2 - The first Brønsted acid catalyzed asymmetric Mukaiyama aldol reaction of aldehydes using silyl enol ethers of ketones as nucleophiles has been reported. A variety of aldehydes and silyl enol ethers of ketones afforded the aldol products in excellent yields and good to excellent enantioselectivities. Mechanistic studies revealed that the actual catalyst may be changed from the silylated Brønsted acid to the Brønsted acid itself depending on the reaction temperature. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/20465277/N_triflylthiophosphoramide_catalyzed_enantioselective_Mukaiyama_aldol_reaction_of_aldehydes_with_silyl_enol_ethers_of_ketones_ L2 - https://doi.org/10.1021/ol100233t DB - PRIME DP - Unbound Medicine ER -