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

Adam McCluskey, James Garner, David J. Young, Shirley Caballero

Research output: Contribution to journalArticle

Abstract

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%).

Original languageEnglish
Pages (from-to)8147-8151
Number of pages5
JournalTetrahedron Letters
Volume41
Issue number42
DOIs
Publication statusPublished - 14 Oct 2000
Externally publishedYes

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