Spectroscopic characterization of (iodomethyl)zinc reagents involved in stereoselective reactions: Spectroscopic evidence that IZnCH2I Is Not Zn(CH2I)2 + ZnI2 in the presence of an ether

Journal of the American Chemical Society

Volumn 118, Issue 19, 1996, Pages 4539-4549

  Charette, André B ^a   Marcoux, Jean François ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

NORBORNANE DERIVATIVE; ZINC COMPLEX;

ARTICLE; CATALYSIS; COMPLEX FORMATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029895546     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja951171k     Document Type: Article

References (42)

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21. Charette, A. B., Marcoux, J. F. Synlett 1995, 1197-1207.
22. Chiral auxiliaries: (a) Charette, A. B.; Côté. B.; Marcoux, J.-F. J. Am. Chem. Soc. 1991, 113, 8166-8167. (b) Charene, A. B.; Marcoux, J.-F.; Côté. B. Tetrahedron Lett. 1991, 32, 7215-7218. (c) Charette, A. B.; Côté, B.; J. Org. Chem. 1993, 58, 933-936. (d) Charette, A. B.; Marcoux, J.-F. Tetrahedron Lett. 1993, 34, 7157-7160. (e) Charette, A. B.; Turcotte, N.; Côté, B. J. Carbohydr. Chem. 1994, 13, 421-432. (f) Charette, A. B.; Turcotte, N.; Marcoux, J.-F. Tetrahedron Lett. 1994, 35, 513-516.
23. Chiral auxiliaries: (a) Charette, A. B.; Côté. B.; Marcoux, J.-F. J. Am. Chem. Soc. 1991, 113, 8166-8167. (b) Charene, A. B.; Marcoux, J.-F.; Côté. B. Tetrahedron Lett. 1991, 32, 7215-7218. (c) Charette, A. B.; Côté, B.; J. Org. Chem. 1993, 58, 933-936. (d) Charette, A. B.; Marcoux, J.-F. Tetrahedron Lett. 1993, 34, 7157-7160. (e) Charette, A. B.; Turcotte, N.; Côté, B. J. Carbohydr. Chem. 1994, 13, 421-432. (f) Charette, A. B.; Turcotte, N.; Marcoux, J.-F. Tetrahedron Lett. 1994, 35, 513-516.
24. Chiral auxiliaries: (a) Charette, A. B.; Côté. B.; Marcoux, J.-F. J. Am. Chem. Soc. 1991, 113, 8166-8167. (b) Charene, A. B.; Marcoux, J.-F.; Côté. B. Tetrahedron Lett. 1991, 32, 7215-7218. (c) Charette, A. B.; Côté, B.; J. Org. Chem. 1993, 58, 933-936. (d) Charette, A. B.; Marcoux, J.-F. Tetrahedron Lett. 1993, 34, 7157-7160. (e) Charette, A. B.; Turcotte, N.; Côté, B. J. Carbohydr. Chem. 1994, 13, 421-432. (f) Charette, A. B.; Turcotte, N.; Marcoux, J.-F. Tetrahedron Lett. 1994, 35, 513-516.
25. Chiral auxiliaries: (a) Charette, A. B.; Côté. B.; Marcoux, J.-F. J. Am. Chem. Soc. 1991, 113, 8166-8167. (b) Charene, A. B.; Marcoux, J.-F.; Côté. B. Tetrahedron Lett. 1991, 32, 7215-7218. (c) Charette, A. B.; Côté, B.; J. Org. Chem. 1993, 58, 933-936. (d) Charette, A. B.; Marcoux, J.-F. Tetrahedron Lett. 1993, 34, 7157-7160. (e) Charette, A. B.; Turcotte, N.; Côté, B. J. Carbohydr. Chem. 1994, 13, 421-432. (f) Charette, A. B.; Turcotte, N.; Marcoux, J.-F. Tetrahedron Lett. 1994, 35, 513-516.
26. Chiral auxiliaries: (a) Charette, A. B.; Côté. B.; Marcoux, J.-F. J. Am. Chem. Soc. 1991, 113, 8166-8167. (b) Charene, A. B.; Marcoux, J.-F.; Côté. B. Tetrahedron Lett. 1991, 32, 7215-7218. (c) Charette, A. B.; Côté, B.; J. Org. Chem. 1993, 58, 933-936. (d) Charette, A. B.; Marcoux, J.-F. Tetrahedron Lett. 1993, 34, 7157-7160. (e) Charette, A. B.; Turcotte, N.; Côté, B. J. Carbohydr. Chem. 1994, 13, 421-432. (f) Charette, A. B.; Turcotte, N.; Marcoux, J.-F. Tetrahedron Lett. 1994, 35, 513-516.
27. Chiral auxiliaries: (a) Charette, A. B.; Côté. B.; Marcoux, J.-F. J. Am. Chem. Soc. 1991, 113, 8166-8167. (b) Charene, A. B.; Marcoux, J.-F.; Côté. B. Tetrahedron Lett. 1991, 32, 7215-7218. (c) Charette, A. B.; Côté, B.; J. Org. Chem. 1993, 58, 933-936. (d) Charette, A. B.; Marcoux, J.-F. Tetrahedron Lett. 1993, 34, 7157-7160. (e) Charette, A. B.; Turcotte, N.; Côté, B. J. Carbohydr. Chem. 1994, 13, 421-432. (f) Charette, A. B.; Turcotte, N.; Marcoux, J.-F. Tetrahedron Lett. 1994, 35, 513-516.
28. Chiral reagent: (g) Charette, A. B.; Juteau, H. J. Am. Chem. Soc. 1994, 116, 2651-2652. (h) Charette, A. B.; Prescott, S.; Brochu, C. J. Org. Chem. 1995, 60, 1081-1083.
29. Chiral reagent: (g) Charette, A. B.; Juteau, H. J. Am. Chem. Soc. 1994, 116, 2651-2652. (h) Charette, A. B.; Prescott, S.; Brochu, C. J. Org. Chem. 1995, 60, 1081-1083.
30. Chiral catalyst: (i) Charette, A. B.; Brochu, C. J Am. Chem. Soc. 1995, 117, 11367-11368.
31. Chiral allylic alcohols: (j) Charette, A. B.; Lebel, H. J. Org. Chem. 1995, 60, 2966-2967.
32. Presented in part at the 210th ACS National Meeting, Chicago, IL, Aug 20-24, 1995: paper ORGN 186.
33. The presence of an ethereal solvent is generally not suitable in these reactions since the reagent is considered to be "delivered" by the proximal hydroxy group (or zinc akoxide). Much lower diastereoselectivities are generally observed when they are carried out in ether. THF, or DME.
34. 2I"-derived reagent.
35. Extensive decomposition and formation of a precipitate are observed if these studies are carried out in the absence of a complexing agent.
36. This correlation was established by comparison with authentic PrZnI prepared from PrI and activated zinc. The singlet at 0.85 ppm corresponds to ethane.
37. 13C (+120 to -30 ppm) NMR spectra are provided in the supporting information.
38. It is interesting to note not only that the intensity of the Etl signals increased at lower temperature but also that small upshield shifts of the signals were observed.
39. 2Zn]. This equilibrium is however too rapid to be observed by NMR: see ref 19.
40. 2I complex (see ref 8b).
41. The signal at 6 ppm is probably due to the presence of ethane arising from the decomposition of these species.
42. The formation of the zinc alkoxide and ethane is instantaneous at that temperature as observed by low-temperature NMR: Côté, B. Ph.D. Thesis, Université de Montréal, 1994.