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

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Title Tetraallylstannane and Weinreb amides: a simple ‘green’ route to N-protected homoallylic alcohols and allyl ketones
Author Young, David; McCluskey, A.; Garner, J.; Caballero, S.
Journal Name Tetrahedron Letters
Year Published 2000
Place of publication UK
Publisher Pergamon
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%).
Peer Reviewed Yes
Published Yes
Alternative URI http://dx.doi.org/10.1016/S0040-4039(00)01408-8
Volume 41
Page from 8147
Page to 8151
ISSN 0040-4039
Date Accessioned 2001-01-01
Date Available 2015-05-11T00:46:21Z
Language en_US
Faculty Faculty of Science, Environment, Engineering and Technology
Subject PRE2009-Science & Technology
URI http://hdl.handle.net/10072/3129
Publication Type Article in Scholarly Refereed Journal
Publication Type Code c1

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