A new copper-catalyzed [3 + 2] cycloaddition: enantioselective coupling of terminal alkynes with azomethine imines to generate five-membered nitrogen heterocycles.
J Am Chem Soc. 2003 Sep 10; 125(36):10778-9.JA

Abstract

A copper-catalyzed method for the regioselective 1,3-dipolar cycloaddition of azomethine imines to terminal alkynes has been developed. Through the use of a chiral phosphaferrocene-oxazoline ligand, a wide range of substrates can be coupled to generate useful heterocycles in very good enantiomeric excess.

Authors+Show Affiliations

Shintani R

Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.

Fu GC

No affiliation info available

MeSH

AlkynesAzo CompoundsCatalysisCopperCyclizationHeterocyclic CompoundsIminesStereoisomerism

Pub Type(s)

Journal Article

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

Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

12952444

Citation

Shintani, Ryo, and Gregory C. Fu. "A New Copper-catalyzed [3 + 2] Cycloaddition: Enantioselective Coupling of Terminal Alkynes With Azomethine Imines to Generate Five-membered Nitrogen Heterocycles." Journal of the American Chemical Society, vol. 125, no. 36, 2003, pp. 10778-9.

Shintani R, Fu GC. A new copper-catalyzed [3 + 2] cycloaddition: enantioselective coupling of terminal alkynes with azomethine imines to generate five-membered nitrogen heterocycles. J Am Chem Soc. 2003;125(36):10778-9.

Shintani, R., & Fu, G. C. (2003). A new copper-catalyzed [3 + 2] cycloaddition: enantioselective coupling of terminal alkynes with azomethine imines to generate five-membered nitrogen heterocycles. Journal of the American Chemical Society, 125(36), 10778-9.

Shintani R, Fu GC. A New Copper-catalyzed [3 + 2] Cycloaddition: Enantioselective Coupling of Terminal Alkynes With Azomethine Imines to Generate Five-membered Nitrogen Heterocycles. J Am Chem Soc. 2003 Sep 10;125(36):10778-9. PubMed PMID: 12952444.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - A new copper-catalyzed [3 + 2] cycloaddition: enantioselective coupling of terminal alkynes with azomethine imines to generate five-membered nitrogen heterocycles. AU - Shintani,Ryo, AU - Fu,Gregory C, PY - 2003/9/4/pubmed PY - 2004/1/14/medline PY - 2003/9/4/entrez SP - 10778 EP - 9 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 125 IS - 36 N2 - A copper-catalyzed method for the regioselective 1,3-dipolar cycloaddition of azomethine imines to terminal alkynes has been developed. Through the use of a chiral phosphaferrocene-oxazoline ligand, a wide range of substrates can be coupled to generate useful heterocycles in very good enantiomeric excess. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/12952444/A_new_copper_catalyzed_[3_+_2]_cycloaddition:_enantioselective_coupling_of_terminal_alkynes_with_azomethine_imines_to_generate_five_membered_nitrogen_heterocycles_ DB - PRIME DP - Unbound Medicine ER -

Tags

A new copper-catalyzed [3 + 2] cycloaddition: enantioselective coupling of terminal alkynes with azomethine imines to generate five-membered nitrogen heterocycles.J Am Chem Soc. 2003 Sep 10; 125(36):10778-9.JA