Stereospecific coupling of α-aminoalkylcuprates with vinyl iodides

Tetrahedron Letters

Volumn 38, Issue 34, 1997, Pages 5937-5940

  Dieter, R Karl ^a   Sharma, Ram R ^a  

^a CLEMSON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ALLYLAMINE DERIVATIVE; NORRUSPOLINE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY; TEMPERATURE;

EID: 0030835278     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01326-9     Document Type: Article

References (20)

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3. (c) Meyers, A. I. Aldrichimica 1985, 18, 59.
4. (d) Gawley, R. E.; Rein, K. in Comprehensive Organic Synthesis Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, Chapter 2.1 and Vol. 3, Chapter 1.2.
5. (a) Dieter, R. K.; Alexander, C. W. Tetrahedron Lett. 1992, 33, 5693.
6. (b) Dieter, R. K.; Alexander, C. W. Synlett 1993, 407.
7. (c) Dieter, R. K.; Dieter, J. W.; Alexander, C. W.; Bhinderwala, N. S. J. Org. Chem. 1996, 61, 2930.
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11. Attempts to prepare acyclic vinyl triflates regio-and stereoselectively from ketone enolates were generally disappointing. For the regio-and stereoselective preparation of ketone enolates see: Fataftah, Z. A.; Kopka, I. E.; Rathke, M. W. J. Am. Chem. Soc. 1980, 702, 3959.
12. For the preparation of the vinyl iodides see: (a) Brown, H. C.; Hamaoka, T.; Ravindran, N. J. Am. Chem. Soc. 1973, 95, 5786; E-1-iodo-1-hexene.
13. (b) Zweifel, G.; Whitney, C. C. Ibid 1967, 89, 2753; E-4-iodo-4-octene.
14. Kim, J.-I. I.; Patel, B. A.; Heck, R. F. J. Org. Chem. 1981, 46, 1067; 2-iodo-1-hexene. This procedure was also used for the preparation of Z -4-iodo-4-octene.
15. Chauhan, Y. S.; Chandraratna, A. S.; Miller, D. A.; Kondrat, R. W.; Reischl, W.; Okamura, W. H. J. Am. Chem. Soc. 1985, 107, 1028.
16. (a) Neukomm, G.; Roessler, F.; Johne, S.; Hesse, M. Planta Medica 1983, 48, 246.
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20. Dieter, R. K.; Li., S. manuscript submitted.