Tandem carbocupration/oxygenation of terminal alkynes

Organic Letters

Volumn 7, Issue 25, 2005, Pages 5681-5683

  Zhang, Donghui ^a   Ready, Joseph M ^a  

^a UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 29444456896     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052413g     Document Type: Article

References (26)

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6. Review: Clarke, M. L. Curr. Org. Chem. 2005, 9, 701-710.
7. An elegant methylalumination/oxidation of terminal olefins has been reported: (a) Shaughnessy, K. H.; Waymouth, R. M. J. Am. Chem. Soc. 1995, 117, 5873-5874.
8. (b) Kondakov, D. Y.; Negishi, E.-i. J. Am. Chem. Soc. 1995, 117, 10771-10772.
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19. Westmijze, H.; Kleijn, H.; Vermeer, P. Tetrahedron Lett. 1977, 2023-2026.
20. 2CuMgBr proceeds with 4.7:1 regioselectivity favoring the 2,2-disubstituted product. However, no products derived from oxidation of the minor regioisomer were detected in the crude carbo-oxygenation reaction mixture. All other carbocuprations occurred with >50:1 selectivity.
21. Identifiable side products include trisubstituted olefin I (ca. 5%), vinyl bromide II (ca. 5%), and dimer 4 (ca. 10%). See also ref 14.
22. - present in the reaction mixture.
23. See Supporting Information for details.
24. (a) Joshi, A. P.; Nayak, U. R.; Dev, S. Tetrahedron 1976, 32, 1423-1425.
25. (b) Syper, L. Tetrahedron 1987, 43, 2853-2871.
26. 4, concentrated, and purified by flash chromatography.