Tetraallylstannane and Weinreb amides: a simple 'green' route to N-protected homoallylic alcohols and allyl ketones

We have explored the addition of tetraallylstannane (7) to a variety of N-p rotected Weinreb amides (N-phthalimido and N-benzyl). Reactions were conduc ted in methanol and the ionic liquid, butyl-methylimidazole tetrafluorobora te (bmim[BF4]), yields of the corresponding N-protected allylketones were m oderate to good. Allylation of the corresponding aminoaldehydes gave excell ent yields of homoallylic alcohols (68-94%) and moderate to good diastereos electivities (50-86%). (C) 2000 Published by Elsevier Science Ltd.