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Organocatalyzed enantioselective protonation of silyl enol ethers: scope, limitations, and application to the preparation of enantioenriched homoisoflavones.
J Org Chem. 2010 Nov 19; 75(22):7704-16.JO

Abstract

In the present work, enantioselective protonation of silyl enol ethers is reported by means of a variety of chiral nitrogen bases as catalysts, mainly derived from cinchona alkaloids, in the presence of various protic nucleophiles as proton source. A detailed study of the most relevant reaction parameters is disclosed allowing high enantioselectivities of up to 92% ee with excellent yields to be achieved under mild and eco-friendly conditions. The synthetic utility of this organocatalytic protonation was demonstrated during the preparation of two homoisoflavones 4a and 4b, isolated from Chlorophytum Inornatum and Scilla Nervosa, which were obtained with 81% and 78% ee, respectively.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Poisson T
Laboratoire de Chimie Organique Bio-organique Réactivité et Analyse (COBRA), CNRS UMR 6014 & FR 3038, Université et INSA de Rouen, Rue Tesnière, Mont-Saint-Aignan 76130-F, France.
Gembus V
No affiliation info available
Dalla V
No affiliation info available
Oudeyer S
No affiliation info available
Levacher V
No affiliation info available

MeSH

CatalysisCinchona AlkaloidsEthersIsoflavonesMolecular StructureSilanesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

20958068

Citation

Poisson, Thomas, et al. "Organocatalyzed Enantioselective Protonation of Silyl Enol Ethers: Scope, Limitations, and Application to the Preparation of Enantioenriched Homoisoflavones." The Journal of Organic Chemistry, vol. 75, no. 22, 2010, pp. 7704-16.
Poisson T, Gembus V, Dalla V, et al. Organocatalyzed enantioselective protonation of silyl enol ethers: scope, limitations, and application to the preparation of enantioenriched homoisoflavones. J Org Chem. 2010;75(22):7704-16.
Poisson, T., Gembus, V., Dalla, V., Oudeyer, S., & Levacher, V. (2010). Organocatalyzed enantioselective protonation of silyl enol ethers: scope, limitations, and application to the preparation of enantioenriched homoisoflavones. The Journal of Organic Chemistry, 75(22), 7704-16. https://doi.org/10.1021/jo101585t
Poisson T, et al. Organocatalyzed Enantioselective Protonation of Silyl Enol Ethers: Scope, Limitations, and Application to the Preparation of Enantioenriched Homoisoflavones. J Org Chem. 2010 Nov 19;75(22):7704-16. PubMed PMID: 20958068.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Organocatalyzed enantioselective protonation of silyl enol ethers: scope, limitations, and application to the preparation of enantioenriched homoisoflavones. AU - Poisson,Thomas, AU - Gembus,Vincent, AU - Dalla,Vincent, AU - Oudeyer,Sylvain, AU - Levacher,Vincent, Y1 - 2010/10/19/ PY - 2010/10/21/entrez PY - 2010/10/21/pubmed PY - 2014/7/19/medline SP - 7704 EP - 16 JF - The Journal of organic chemistry JO - J Org Chem VL - 75 IS - 22 N2 - In the present work, enantioselective protonation of silyl enol ethers is reported by means of a variety of chiral nitrogen bases as catalysts, mainly derived from cinchona alkaloids, in the presence of various protic nucleophiles as proton source. A detailed study of the most relevant reaction parameters is disclosed allowing high enantioselectivities of up to 92% ee with excellent yields to be achieved under mild and eco-friendly conditions. The synthetic utility of this organocatalytic protonation was demonstrated during the preparation of two homoisoflavones 4a and 4b, isolated from Chlorophytum Inornatum and Scilla Nervosa, which were obtained with 81% and 78% ee, respectively. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/20958068/Organocatalyzed_enantioselective_protonation_of_silyl_enol_ethers:_scope_limitations_and_application_to_the_preparation_of_enantioenriched_homoisoflavones_ L2 - https://doi.org/10.1021/jo101585t DB - PRIME DP - Unbound Medicine ER -