4-(Trialkylsilyl)oxybut-2-ynals as dienophiles in the Diels–Alder synthesis of α-(hydroxymethyl)benzaldehydes

The α-(hydroxymethyl)benzaldehyde derivative 2 has been synthesized by heating ynal 3 with diene 5 , which produced the α-(silyloxymethyl)benzaldehyde 6 by a Diels–Alder/ retro-Diels–Alder process, followed by methylation, thioacetalization, and removal of the silyl protecting group. Decarbonylation...

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Bibliographic Details
Published in:Tetrahedron letters 2001-10, Vol.42 (42), p.7367-7369
Main Authors: Morrison, Christopher F, Burnell, D.Jean
Format: Article
Language:English
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Summary:The α-(hydroxymethyl)benzaldehyde derivative 2 has been synthesized by heating ynal 3 with diene 5 , which produced the α-(silyloxymethyl)benzaldehyde 6 by a Diels–Alder/ retro-Diels–Alder process, followed by methylation, thioacetalization, and removal of the silyl protecting group. Decarbonylation of α-(silyloxymethyl)benzaldehydes 6 and 10 takes place readily in the presence of zinc(II) chloride or para-toluenesulfonic acid. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(01)01541-6