Custom synthesis of substituted butenolides, dihydropyranones, and α-E-alkylidenelactones via alkenylalumination

Alkenylalumination of aldehydes with [α-(ethoxycarbonyl)-β-(t-butyldimethylsilyloxyalkyl)alkenyl]diisobutylaluminum provides the corresponding α-Z-alkylidene-β′-hydroxy esters, which upon protection and treatment with trifluoroacetic acid lactonizes to furnish α-acetoxyalkyl butenolides (n=1) and di...

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Bibliographic Details
Published in:Tetrahedron letters 2011-09, Vol.52 (39), p.4985-4988
Main Authors: Veeraraghavan Ramachandran, P., Pratihar, Debarshi, Garner, Garrett, China Raju, B.
Format: Article
Language:English
Subjects:
1,4-Addition
Alkenylalumination
Butenolides
Chemistry
Dihydropyranones
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Lactones
Organic chemistry
Preparations and properties
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Summary:Alkenylalumination of aldehydes with [α-(ethoxycarbonyl)-β-(t-butyldimethylsilyloxyalkyl)alkenyl]diisobutylaluminum provides the corresponding α-Z-alkylidene-β′-hydroxy esters, which upon protection and treatment with trifluoroacetic acid lactonizes to furnish α-acetoxyalkyl butenolides (n=1) and dihydropyranones (n=2) in 40% overall yield. Conjugate addition to these lactenones and concurrent acetate elimination constitute a general and stereospecific synthesis of the corresponding α-E-alkylidene lactones.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.06.103