3-Cuprio-2-pyrone: An Extraordinary Organocopper Reagent

Journal of Organic Chemistry

Volumn 50, Issue 25, 1985, Pages 5041-5044

  Posner, Gary H ^a   Harrison, W ^a   Wettlaufer, David G ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0343970674     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00225a008     Document Type: Article

References (30)

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5. For a similar reactivity pattern of cyanomethylcopper, see: Corey, E. J.; Kuwajima, I. Tetrahedron Lett. 1972, 487.
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9. For Sn 2' regioselectivity in organocopper alkylation of allylic alcohols and carboxylates, see: (a) Goering, H. L.; Kantner, S. S. J. Org. Chem. 1981, 46, 2144; J. Am. Chem. Soc. 1984, 49, 422. (b) Goering, H. L.; Tseng, C. C. J. Am. Chem. Soc. 1985, 50, 1597. (c) Cf.: Marshall, J. A.; Audia, V. H. J. Am. Chem. Soc. 1985, 50, 1607. (d) For another study of this butenyl system with Cu(I) species involving completely ionic intermediates, see: Lane, J. F.; Fentress, J.; Sherwood, L. T., Jr. J. Am. Chem. Soc. 1944, 66, 545.
10. Cf.: Kitagawa, Y.; Hashimoto, S.; Iemura, S.; Yamanoto, H.; Nozaki, H. J. Am. Chem. Soc. 1976, 98, 5030.
11. That such copper-olefin π-complexation influences the regiochemistry of allylic substitution by organocopper reagents has precedent in the work of Goering and Marshall (ref 11). For other evidence supporting copper-enone π-complexation, see: Kraus, S. R.; Smith, S. G. J. Am. Chem. Soc. 1981, 103, 141. Hallnemo, G.; Olsson, T.; Ullenius, C. J. Organomet. Chem. 1985, 282, 133.
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