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Pd-catalyzed asymmetric allylic alkylation of pyrazol-5-ones with allylic alcohols: the role of the chiral phosphoric acid in C-O bond cleavage and stereocontrol.
J Am Chem Soc. 2013 Jun 26; 135(25):9255-8.JA

Abstract

The combination of a palladium complex with a chiral phosphoramidite ligand and a chiral phosphoric acid enables the first highly efficient asymmetric allylic alkylation of pyrazol-5-ones with allylic alcohols, affording multiply functionalized heterocyclic products in high yields with excellent enantioselectivities that would be of great potential in the synthesis of pharmaceutically interesting molecules.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Tao ZL
Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, China.
Zhang WQ
No affiliation info available
Chen DF
No affiliation info available
Adele A
No affiliation info available
Gong LZ
No affiliation info available

MeSH

AlkylationAllyl CompoundsCatalysisMolecular StructureOrganometallic CompoundsPalladiumPhosphoric AcidsPropanolsPyrazolonesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

23734612

Citation

Tao, Zhong-Lin, et al. "Pd-catalyzed Asymmetric Allylic Alkylation of Pyrazol-5-ones With Allylic Alcohols: the Role of the Chiral Phosphoric Acid in C-O Bond Cleavage and Stereocontrol." Journal of the American Chemical Society, vol. 135, no. 25, 2013, pp. 9255-8.
Tao ZL, Zhang WQ, Chen DF, et al. Pd-catalyzed asymmetric allylic alkylation of pyrazol-5-ones with allylic alcohols: the role of the chiral phosphoric acid in C-O bond cleavage and stereocontrol. J Am Chem Soc. 2013;135(25):9255-8.
Tao, Z. L., Zhang, W. Q., Chen, D. F., Adele, A., & Gong, L. Z. (2013). Pd-catalyzed asymmetric allylic alkylation of pyrazol-5-ones with allylic alcohols: the role of the chiral phosphoric acid in C-O bond cleavage and stereocontrol. Journal of the American Chemical Society, 135(25), 9255-8. https://doi.org/10.1021/ja402740q
Tao ZL, et al. Pd-catalyzed Asymmetric Allylic Alkylation of Pyrazol-5-ones With Allylic Alcohols: the Role of the Chiral Phosphoric Acid in C-O Bond Cleavage and Stereocontrol. J Am Chem Soc. 2013 Jun 26;135(25):9255-8. PubMed PMID: 23734612.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Pd-catalyzed asymmetric allylic alkylation of pyrazol-5-ones with allylic alcohols: the role of the chiral phosphoric acid in C-O bond cleavage and stereocontrol. AU - Tao,Zhong-Lin, AU - Zhang,Wen-Quan, AU - Chen,Dian-Feng, AU - Adele,Arafate, AU - Gong,Liu-Zhu, Y1 - 2013/06/14/ PY - 2013/6/6/entrez PY - 2013/6/6/pubmed PY - 2014/1/15/medline SP - 9255 EP - 8 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 135 IS - 25 N2 - The combination of a palladium complex with a chiral phosphoramidite ligand and a chiral phosphoric acid enables the first highly efficient asymmetric allylic alkylation of pyrazol-5-ones with allylic alcohols, affording multiply functionalized heterocyclic products in high yields with excellent enantioselectivities that would be of great potential in the synthesis of pharmaceutically interesting molecules. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/23734612/Pd_catalyzed_asymmetric_allylic_alkylation_of_pyrazol_5_ones_with_allylic_alcohols:_the_role_of_the_chiral_phosphoric_acid_in_C_O_bond_cleavage_and_stereocontrol_ L2 - https://doi.org/10.1021/ja402740q DB - PRIME DP - Unbound Medicine ER -