Nickel(0)-catalyzed asymmetric hydrocyanation of 1,3-dienes

Organic Letters

Volumn 8, Issue 20, 2006, Pages 4657-4659

  Saha, Biswajit ^a   RajanBabu, T V ^a  

^a OHIO STATE UNIVERSITY   (United States)

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[No Author keywords available]

Indexed keywords

EID: 33750050300     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062002f     Document Type: Article

References (32)

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10. For more recent results, see: (c) Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012 and references therein.
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24. See the Supporting Information for details including precautions to be undertaken when using HCN as a reagent.
25. Toxicity of Hydrogen Cyanide. Hydrogen cyanide is a highly toxic, volatile liquid (bp 27 °C) that is also susceptible to explosive polymerization in the presence of base catalysts. It should be handled only in a well-ventilated fume hood or drybox. Sensible precautions include not working alone and having available proper first aid equipment. When handling large quantities of HCN, it should be handled by a team of at least two technically qualified individuals who have received appropriate medical training for treating HCN poisoning (for details see: Prudent Practices for Handling Hazardous Chemicals in Laboratories; National Academy Press: Washington, DC, 1981; pp 45-47).
26. 5 to ∼100 mL of the above solution. Excess HCN maybe disposed of by burning or in the case of small amounts by addition to aqueous sodium hypochlorite (which converts it to the cyanate). In the present case, no more than 2 mmol (2 mL of toluene solution) was used at one time.
27. For the use of asymmetric hydrovinylation in this context, see: Zhang, A.; RajanBabu, T. V. J. Am. Chem. Soc. 2006, 128, 54.
28. For a more complete list, see the Supporting Information.
29. (a) RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101.
30. (b) Rh-catalyzed hydrogenation: RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012.
31. (c) Pd-catalyzed allylation: Clyne, D. S.; Mermet-Bouvier, Y. C.; Nomura, N.; RajanBabu, T. V. J. Org. Chem. 1999, 64, 7601.
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