The stereochemistry of 1,2-additions of allylmagnesium, allylindium, and allylbismuth to cyclohexenones

Tetrahedron Letters

Volumn 47, Issue 19, 2006, Pages 3291-3294

  Zhao, Liang ^a   Burnell, D Jean ^a  

^a DALHOUSIE UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE DERIVATIVE; BISMUTH DERIVATIVE; CARVONE; INDIUM; MAGNESIUM DERIVATIVE;

ARTICLE; METHYLATION; STEREOCHEMISTRY;

EID: 33645784188     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.03.034     Document Type: Article

References (27)

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13. 3, 80 MHz instrument): δ 70.7, 48.1, 46.8, 37.5, 32.4, 27.6, 22.6, 16.4, 14.8.
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17. Allylindium procedure: Indium metal (0.50 mmol) and allyl iodide (0.75 mmol) in DMF (2.0 mL) were stirred under argon for 1 h during which time most of the indium dissolved giving a grey solution. The enone (0.50 mmol) in DMF (1.0 mL) was introduced dropwise, and the solution was stirred at room temperature. Reaction progress was monitored by TLC. Aqueous workup provided the product(s). The ratio of products was determined by NMR.
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22. 4), and the ether was evaporated under vacuum. The ratio of products was determined by NMR.
23. 13C NMR: δ 149.6 (0), 134.3 (1), 124.1 (1), 118.4 (2), 69.3 (0), 56.4 (1), 56.3 (1), 54.5 (1), 47.6 (2), 42.7 (0), 40.1 (2), 39.7 (2), 37.8 (0), 36.4 (2), 36.1 (1), 36.0 (1), 33.5 (2), 32.9 (2), 32.7 (2), 32.2 (2), 28.4 (2), 28.2 (1), 24.5 (2), 24.1 (2), 23.0 (3), 22.8 (3), 21.7 (2), 18.9 (3), 18.1 (3), 12.2 (3).
24. 1,2-Addition of an allylindium reagent to carvone was reported previously:. Kim H.Y., Choi K.I., Pae A.N., Koh H.Y., Choi J.H., and Cho Y.S. Synth. Commun. 33 (2003) 1899-1904 but the stereochemistry of the product was not determined
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26. 13C NMR: δ 149.3, 137.7, 136.6, 135.2, 133.7, 132.9, 128.1, 128.0, 127.9, 127.8, 126.1, 125.7, 125.5, 125.4, 117.4 (2), 109.0 (2), 80.5 (0), 64.1 (2), 43.9 (2), 39.7 (1), 34.7 (2), 31.2 (2), 21.1 (3), 17.6 (3).
27. Zhao L., and Burnell D.J. Org. Lett. 8 (2006) 155-157