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Copper-catalyzed asymmetric addition of arylboronates to isatins: a catalytic cycle involving alkoxocopper intermediates.
Chem Commun (Camb). 2010 Sep 28; 46(36):6822-4.CC

Abstract

A copper-catalyzed addition of arylboronates to isatins has been developed to give 3-aryl-3-hydroxy-2-oxindoles under mild conditions. The catalytic cycle of this process has been examined through a series of stoichiometric reactions and an effective asymmetric variant has also been described by the use of a chiral N-heterocyclic carbene ligand.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Shintani R
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan. shintani@kuchem.kyoto-u.ac.jp
Takatsu K
No affiliation info available
Hayashi T
No affiliation info available

MeSH

Boronic AcidsCatalysisCopperCrystallography, X-RayIndolesIsatinLigandsMethaneMolecular ConformationOxindolesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

20725672

Citation

Shintani, Ryo, et al. "Copper-catalyzed Asymmetric Addition of Arylboronates to Isatins: a Catalytic Cycle Involving Alkoxocopper Intermediates." Chemical Communications (Cambridge, England), vol. 46, no. 36, 2010, pp. 6822-4.
Shintani R, Takatsu K, Hayashi T. Copper-catalyzed asymmetric addition of arylboronates to isatins: a catalytic cycle involving alkoxocopper intermediates. Chem Commun (Camb). 2010;46(36):6822-4.
Shintani, R., Takatsu, K., & Hayashi, T. (2010). Copper-catalyzed asymmetric addition of arylboronates to isatins: a catalytic cycle involving alkoxocopper intermediates. Chemical Communications (Cambridge, England), 46(36), 6822-4. https://doi.org/10.1039/c0cc01635g
Shintani R, Takatsu K, Hayashi T. Copper-catalyzed Asymmetric Addition of Arylboronates to Isatins: a Catalytic Cycle Involving Alkoxocopper Intermediates. Chem Commun (Camb). 2010 Sep 28;46(36):6822-4. PubMed PMID: 20725672.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Copper-catalyzed asymmetric addition of arylboronates to isatins: a catalytic cycle involving alkoxocopper intermediates. AU - Shintani,Ryo, AU - Takatsu,Keishi, AU - Hayashi,Tamio, Y1 - 2010/08/20/ PY - 2010/8/21/entrez PY - 2010/8/21/pubmed PY - 2010/12/28/medline SP - 6822 EP - 4 JF - Chemical communications (Cambridge, England) JO - Chem Commun (Camb) VL - 46 IS - 36 N2 - A copper-catalyzed addition of arylboronates to isatins has been developed to give 3-aryl-3-hydroxy-2-oxindoles under mild conditions. The catalytic cycle of this process has been examined through a series of stoichiometric reactions and an effective asymmetric variant has also been described by the use of a chiral N-heterocyclic carbene ligand. SN - 1364-548X UR - https://www.unboundmedicine.com/medline/citation/20725672/Copper_catalyzed_asymmetric_addition_of_arylboronates_to_isatins:_a_catalytic_cycle_involving_alkoxocopper_intermediates_ L2 - https://doi.org/10.1039/c0cc01635g DB - PRIME DP - Unbound Medicine ER -