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Anti carbocyanative cyclization of enynes under nickel catalysis.
J Org Chem. 2013 May 03; 78(9):4366-72.JO

Abstract

Anti carbocyanative cyclization using 1,6-enynes under nickel catalysis is described. This reaction is triggered by hydronickelation to alkenes followed by carbometalation. Steric repulsion caused by the bulky substituents on alkynes promotes isomerization of the carbon-carbon double bond geometry in an organonickel intermediate to introduce both alkyl and cyano groups in an anti fashion.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Igarashi T
Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba 260-8675, Japan.
Arai S
No affiliation info available
Nishida A
No affiliation info available

MeSH

AlkenesAlkynesCatalysisCyanatesCyclizationMolecular StructureNickelOrganometallic CompoundsStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

23570365

Citation

Igarashi, Tomohiro, et al. "Anti Carbocyanative Cyclization of Enynes Under Nickel Catalysis." The Journal of Organic Chemistry, vol. 78, no. 9, 2013, pp. 4366-72.
Igarashi T, Arai S, Nishida A. Anti carbocyanative cyclization of enynes under nickel catalysis. J Org Chem. 2013;78(9):4366-72.
Igarashi, T., Arai, S., & Nishida, A. (2013). Anti carbocyanative cyclization of enynes under nickel catalysis. The Journal of Organic Chemistry, 78(9), 4366-72. https://doi.org/10.1021/jo400342y
Igarashi T, Arai S, Nishida A. Anti Carbocyanative Cyclization of Enynes Under Nickel Catalysis. J Org Chem. 2013 May 3;78(9):4366-72. PubMed PMID: 23570365.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Anti carbocyanative cyclization of enynes under nickel catalysis. AU - Igarashi,Tomohiro, AU - Arai,Shigeru, AU - Nishida,Atsushi, Y1 - 2013/04/18/ PY - 2013/4/11/entrez PY - 2013/4/11/pubmed PY - 2013/12/18/medline SP - 4366 EP - 72 JF - The Journal of organic chemistry JO - J Org Chem VL - 78 IS - 9 N2 - Anti carbocyanative cyclization using 1,6-enynes under nickel catalysis is described. This reaction is triggered by hydronickelation to alkenes followed by carbometalation. Steric repulsion caused by the bulky substituents on alkynes promotes isomerization of the carbon-carbon double bond geometry in an organonickel intermediate to introduce both alkyl and cyano groups in an anti fashion. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/23570365/Anti_carbocyanative_cyclization_of_enynes_under_nickel_catalysis_ L2 - https://doi.org/10.1021/jo400342y DB - PRIME DP - Unbound Medicine ER -