Tetrahedron p. 7839 - 7856 (1992)
Update date:2022-08-03
Topics:
Davies, D. Huw
Haire, Nicholas A.
Hall, Jonathan
Smith, Edward H.
Reaction of the allyl anions of O-trialkylsilyl-N-alkyl-2-(1'-hydroxyprop-2'-enyl)imidazoles with aldehydes and ketones gives products of α- and γ-attack.Greater steric hindrance in the anion (triisopropyl vs t-butyldimethylsilyl) and in the aldehyde or ketone favours the γ-products.Sequential desilylation, N-methylation and treatment with base resulted in cleavage of these products to γ-lactones.The method was applied to the synthesis of (+/-)-cavernosine.
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