Nickel-Catalyzed highly chemo-, Regio-, and stereoselective three-component reaction of norbornene with two alkynes

Organic Letters

Volumn 12, Issue 1, 2010, Pages 148-151

  Ogata, Kenichi ^a   Sugasawa, Jun ^a   Atsuumi, Yuka ^a   Fukuzawa, Shin Ichi ^a  

^a CHUO UNIVERSITY   (Japan)

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EID: 73949083933     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9025556     Document Type: Article

References (30)

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19. (b) Ogata, K.; Sugasawa, J.; Fukuzawa, S.-i. Angew. Chem., Int. Ed. 2009, 48, 6078.
20. The signal assigned to the alkenyl- and alkynyl-substituted endo proton was observed as a doublet due to the coupling with each other (ca. 9 Hz), and no coupling was observed with the bridgehead proton. These observations support the exo,exo structure of 4. See: (a) Nishihara, Y.; Inoue, Y.; Itazaki, M.; Takagi, K. Org. Lett. 2005, 7, 2639.
21. (b) Caltskan, R.; Ali, M. F.; Sahin, E.; Watson, W. H.; Balci, M. J. Org. Chem. 2007, 72, 3353.
22. The corresponding 1,5-enyne which possesses a tert-butyldimethylsilyl group was obtained in 33% isolated yield (A/B = 93:7).
23. Corresponding 1,5-enyne 41a which possesses a cyclohexyl group was obtained in 28% isolated yield (A/B = 79:21).
24. In this reaction, the hydroalkynylation product of norbornadiene was obtained in 42% isolated yield.
25. Phosphine screening results for reaction between two molecules of 1 and 3c are shown in the Supporting Information.
26. 1H NMR because it is difficult to separate compound 5a and small amounts of byproduct (homodimer of 1).
27. 2/phosphine by the reaction with terminal alkyne is usually postulated. See: Ogoshi, S.; Ueta, M.; Oka, M.; Kurosawa, H. Chem. Commun. 2004, 2732, and refs If, 6-8, and 9.
28. (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596.
29. (b) Bock, V. D.; Hiemstra, H.; van Maarseveen, J. H. Eur. J. Org. Chem. 2006, 51.
30. The supplementary crystallographic data of 9 (CCDC number, 749875) can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.uk/data-request/cif.