Enantioselective Cyclopropanation of Allylic Alcohols. The Effect of Zinc Iodide

Journal of Organic Chemistry

Volumn 62, Issue 10, 1997, Pages 3375-3389

  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: 1542713051     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9702397     Document Type: Article

References (60)

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48. 1H-NMR analysis.
49. 2 in situ avoids this tedious procedure.
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51. Independent generation of the iodomethylzinc alkoxide of cinnamyl alcohol followed by cyclopropanation under standard conditions using 10 mol % of 7 led to 8 in a very unselective manner (2% ee). This suggested that the reason route 4 was so poorly selective resulted from the formation of diiodomethane and that this compound reacted with the ethylzinc alkoxide of cinnamyl alcohol to form the (iodomethyl)zinc alkoxide.
52. 2:
53. 2:
54. 2:
55. 2:
56. 2:
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