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Group 11 metal amide-catalyzed asymmetric cycloaddition reactions of azomethine imines with terminal alkynes.
J Am Chem Soc. 2012 Dec 12; 134(49):20049-52.JA

Abstract

We developed a 1,3-dipolar cycloaddition reaction of azomethine imines with terminal alkynes catalyzed by group 11 metal amides to provide N,N-bicyclic pyrazolidinone derivatives. This reaction afforded the cycloadducts in a unique 5,7-disubstituted manner. Furthermore, we succeeded in applying this catalysis to asymmetric reactions, and the desired heterocycles were produced in high yields with exclusive regioselectivity and high enantioselectivity. Mechanistic studies elucidated a stepwise reaction pathway and critical features that determine the regioselectivity.

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Authors+Show Affiliations

Imaizumi T
Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Yamashita Y
No affiliation info available
Kobayashi S
No affiliation info available

MeSH

AlkynesAmidesAzo CompoundsCatalysisCyclizationIminesMolecular StructureOrganometallic CompoundsPyrazolesThiosemicarbazonesTransition Elements

Pub Type(s)

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

Language

eng

PubMed ID

23194467

Citation

Imaizumi, Takaki, et al. "Group 11 Metal Amide-catalyzed Asymmetric Cycloaddition Reactions of Azomethine Imines With Terminal Alkynes." Journal of the American Chemical Society, vol. 134, no. 49, 2012, pp. 20049-52.
Imaizumi T, Yamashita Y, Kobayashi S. Group 11 metal amide-catalyzed asymmetric cycloaddition reactions of azomethine imines with terminal alkynes. J Am Chem Soc. 2012;134(49):20049-52.
Imaizumi, T., Yamashita, Y., & Kobayashi, S. (2012). Group 11 metal amide-catalyzed asymmetric cycloaddition reactions of azomethine imines with terminal alkynes. Journal of the American Chemical Society, 134(49), 20049-52. https://doi.org/10.1021/ja311150n
Imaizumi T, Yamashita Y, Kobayashi S. Group 11 Metal Amide-catalyzed Asymmetric Cycloaddition Reactions of Azomethine Imines With Terminal Alkynes. J Am Chem Soc. 2012 Dec 12;134(49):20049-52. PubMed PMID: 23194467.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Group 11 metal amide-catalyzed asymmetric cycloaddition reactions of azomethine imines with terminal alkynes. AU - Imaizumi,Takaki, AU - Yamashita,Yasuhiro, AU - Kobayashi,Shū, Y1 - 2012/12/04/ PY - 2012/12/1/entrez PY - 2012/12/1/pubmed PY - 2013/6/6/medline SP - 20049 EP - 52 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 134 IS - 49 N2 - We developed a 1,3-dipolar cycloaddition reaction of azomethine imines with terminal alkynes catalyzed by group 11 metal amides to provide N,N-bicyclic pyrazolidinone derivatives. This reaction afforded the cycloadducts in a unique 5,7-disubstituted manner. Furthermore, we succeeded in applying this catalysis to asymmetric reactions, and the desired heterocycles were produced in high yields with exclusive regioselectivity and high enantioselectivity. Mechanistic studies elucidated a stepwise reaction pathway and critical features that determine the regioselectivity. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/23194467/Group_11_metal_amide_catalyzed_asymmetric_cycloaddition_reactions_of_azomethine_imines_with_terminal_alkynes_ L2 - https://doi.org/10.1021/ja311150n DB - PRIME DP - Unbound Medicine ER -