A highly regioselective indium-mediated allylation of pyridine derivatives: synthesis of (±)-dihydropinidine from pyridine
✍ Scribed by Teck-Peng Loh; Pek-Ling Lye; Rui-Bin Wang; Keng-Yeow Sim
- Publisher
- Elsevier Science
- Year
- 2000
- Tongue
- French
- Weight
- 72 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The preparation of various 1-acyl-1,2-dihydropyridines with high regioselectivity by indium-mediated allylation of the corresponding 1-acylpyridinium salts is demonstrated. This is applied to the synthesis of (±)-dihydropinidines.
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Linear a homoallylic alcohol adducts were obtained with high regioselectivities in moderate to good yields using allylic indium reagents in the presence of 10 M water. The exceptionally high regioselectivities observed were neither steric nor electronic in origin from the results presented in this p
N-Ethoxycarbonylpyridinium chloride (A) reacted with RCu. BF3 at 4position with almost complete regioselectivity ( better than 99% ) to afford the corre-
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Allyl indium, prepared from allyl bromide and indium metal in THF, reacts with terminal epoxides at room temperature to afford the corresponding bishomoallyl alcohols in excellent yields and with good regioselectivity.