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

doi:10.1016/S0040-4039(00)01408-8

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 journal › Article

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 language	English
Pages (from-to)	8147-8151
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Issue number	42
DOIs	https://doi.org/10.1016/S0040-4039(00)01408-8
Publication status	Published - 14 Oct 2000
Externally published	Yes

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10.1016/S0040-4039(00)01408-8

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

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%).",

keywords = "Allyl ketones, Green chemistry, Homoallylic alcohols, Tetraallylstannane, Weinreb amides",

author = "Adam McCluskey and James Garner and Young, {David J.} and Shirley Caballero",

year = "2000",

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T1 - Tetraallylstannane and Weinreb amides

T2 - A simple 'green' route to N-protected homoallylic alcohols and allyl ketones

AU - McCluskey, Adam

AU - Garner, James

AU - Young, David J.

AU - Caballero, Shirley

PY - 2000/10/14

Y1 - 2000/10/14

N2 - 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%).

AB - 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%).

KW - Allyl ketones

KW - Green chemistry

KW - Homoallylic alcohols

KW - Tetraallylstannane

KW - Weinreb amides

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JF - Tetrahedron Letters: the international journal for the rapid publication of all preliminary communications in organic chemistry

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