Tetraallylstannane and Weinreb amides: a simple ‘green’ route to N-protected homoallylic alcohols and allyl ketones
Author(s)
Young, David
McCluskey, A.
Garner, J.
Caballero, S.
Griffith University Author(s)
Year published
2000
Metadata
Show full item recordAbstract
We have explored the addition of tetraallylstannane (7) to a variety of N-protected Weinreb amides (N-phthalimido and N-benzyl). Reactions were conducted in methanol and the ionic liquid, butylmethylimidazole tetrafluoroborate (bmim[BF4]), yields of the corresponding N-protected allylketones were moderate to good. Allylation of the corresponding aminoaldehydes gave excellent yields of homoallylic alcohols (68-94%) and moderate to good diastereoselectivities (50-86%).We have explored the addition of tetraallylstannane (7) to a variety of N-protected Weinreb amides (N-phthalimido and N-benzyl). Reactions were conducted in methanol and the ionic liquid, butylmethylimidazole tetrafluoroborate (bmim[BF4]), yields of the corresponding N-protected allylketones were moderate to good. Allylation of the corresponding aminoaldehydes gave excellent yields of homoallylic alcohols (68-94%) and moderate to good diastereoselectivities (50-86%).
View less >
View less >
Journal Title
Tetrahedron Letters
Volume
41
Subject
History and Archaeology
Medicinal and Biomolecular Chemistry
Organic Chemistry