Catalytic, Enantioselective Cyclopropanation of Allylic Alcohols. Substrate Generality

Journal of Organic Chemistry

Volumn 62, Issue 3, 1997, Pages 584-594

  Denmark, Scott E ^a   O'Connor, Stephen P ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001469016     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961859v     Document Type: Article

References (54)

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34. While it is conceivable that bis(iodomethyl)zinc could also form alkoxides, the results were less than encouraging. The reaction of cinnamyl alcohol with 2 equiv of preformed bis(iodomethyl)zinc proceeded very slowly and, in the presence of 0.1 equiv of 7, was also less selective. Either deprotonation is not taking place or the (iodomethyl)zinc alkoxide that is formed is much less reactive than the corresponding ethylzinc alkoxide.
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37. (a) ( - )-17 has been assigned as (1R,2R), Keiderling, T. A.; Yasui, S. C. J. Am. Chem. Soc. 1987, 109, 2311. Sugita, T.; Inouye, Y. Bull. Chem. Soc. Jpn. 1966, 39, 1075.
38. (a) ( - )-17 has been assigned as (1R,2R), Keiderling, T. A.; Yasui, S. C. J. Am. Chem. Soc. 1987, 109, 2311. Sugita, T.; Inouye, Y. Bull. Chem. Soc. Jpn. 1966, 39, 1075.
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41. Careful monitoring of the reactions with and without added zinc iodide have shown a time dependence of enantioselectivity along with the elimination of the induction period.
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46. (b) We wish to thank Professor Seebach for kindly providing us with the details of their diethylzinc distillation.
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48. 3 is tetrameric in benzene: Coates, G. E.; Ridley, D. J. Chem. Soc. 1965, 1870.
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51. 3 is tetrameric in the solid state. X-ray structures : (a) Shearer, H. M. M.; Spencer, C. B. Chem. Commun. 1966, 194. (b) Shearer, H. M. M.; Spencer, C. B. Acta Crystallogr., Sect. B: Crystallogr. Cryst. Chem. 1980, 36, 2046.
52. We have attempted to grow crystals of a variety of bissulfonamides such as 31 with various combinations of solvent, temperature, concentration, and by the addition of both mono- and bidentate ligands for zinc (i.e., TMEDA). Invariably, no crystals were formed, and the solutions became viscous and gellike or a fine powder was formed. This suggests to us that the sulfonamide-zinc species such as 48 are self-associating to form polymeric networks. The zinc of one sulfonamide-zinc complex can be envisioned to coordinate the sulfonyl oxygen of another followed by additional such interactions to form a large networklike structure.
53. (a) Denmark, S. E.; O'Connor, S. P. J. Am. Chem. Soc., manuscript submitted.
54. (b) Charette, A. B.; Marcoux, J.-F. J. Am. Chem. Soc. 1996, 118, 4539.