Solvent-mediated allylation of carbonyl compounds with allylic stannanes

…, PJ Harvey, RL Marshall, A McCluskey…

Index: Cokley, Teresa M.; Harvey, Peta J.; Marshall, Raymond L.; McCluskey, Adam; Young, David J. Journal of Organic Chemistry, 1997 , vol. 62, # 7 p. 1961 - 1964

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Citation Number: 56

Abstract

Methanol promotes the addition of allyltrimethylstannane (1a) to isobutyraldehyde (2a, 30° C) yielding the corresponding homoallylic alcohol (3a), without the necessity for added catalyst. The corresponding reaction of aldehydes 2a-e or activated ketone 2f with tetraallyltin (1b, 0.25 equiv) is substantially faster and proceeds in high yield (81-98%) and with easy separation of the product from tin residues. Aliphatic ketones 2g and 2h also ...