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Regio- and enantioselective Pd-catalyzed allylic alkylation of ketones through allyl enol carbonates.
J Am Chem Soc. 2005 Mar 09; 127(9):2846-7.JA

Abstract

The Pd-catalyzed reorganization of enol allyl carbonates to allylated ketones occurs asymmetrically in the presence of chiral ligands previously developed in this group. With 2-methylcyclohexanone, asymmetric regioselective alkylation occurs at the more substituted carbon without complications of polyalkylation. Alkylation to create quaternary centers in indanones and benzonabenone occurs in much higher ee than using tin or lithium enolates. The sense of enantioinduction in tetralones is opposite from the tin and lithium enolate examples. For the first time, asymmetric creation of tertiary centers occurs with high ee (78-99%). The different results between this reaction and the use of lithium or tin enolates suggest different mechanisms may be involved.

Authors+Show Affiliations

Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA.No affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

15740108

Citation

Trost, Barry M., and Jiayi Xu. "Regio- and Enantioselective Pd-catalyzed Allylic Alkylation of Ketones Through Allyl Enol Carbonates." Journal of the American Chemical Society, vol. 127, no. 9, 2005, pp. 2846-7.
Trost BM, Xu J. Regio- and enantioselective Pd-catalyzed allylic alkylation of ketones through allyl enol carbonates. J Am Chem Soc. 2005;127(9):2846-7.
Trost, B. M., & Xu, J. (2005). Regio- and enantioselective Pd-catalyzed allylic alkylation of ketones through allyl enol carbonates. Journal of the American Chemical Society, 127(9), 2846-7.
Trost BM, Xu J. Regio- and Enantioselective Pd-catalyzed Allylic Alkylation of Ketones Through Allyl Enol Carbonates. J Am Chem Soc. 2005 Mar 9;127(9):2846-7. PubMed PMID: 15740108.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Regio- and enantioselective Pd-catalyzed allylic alkylation of ketones through allyl enol carbonates. AU - Trost,Barry M, AU - Xu,Jiayi, PY - 2005/3/3/pubmed PY - 2005/4/21/medline PY - 2005/3/3/entrez SP - 2846 EP - 7 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 127 IS - 9 N2 - The Pd-catalyzed reorganization of enol allyl carbonates to allylated ketones occurs asymmetrically in the presence of chiral ligands previously developed in this group. With 2-methylcyclohexanone, asymmetric regioselective alkylation occurs at the more substituted carbon without complications of polyalkylation. Alkylation to create quaternary centers in indanones and benzonabenone occurs in much higher ee than using tin or lithium enolates. The sense of enantioinduction in tetralones is opposite from the tin and lithium enolate examples. For the first time, asymmetric creation of tertiary centers occurs with high ee (78-99%). The different results between this reaction and the use of lithium or tin enolates suggest different mechanisms may be involved. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/15740108/Regio__and_enantioselective_Pd_catalyzed_allylic_alkylation_of_ketones_through_allyl_enol_carbonates_ L2 - https://doi.org/10.1021/ja043472c DB - PRIME DP - Unbound Medicine ER -
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