Abstract

Secondary sugar allyltin derivatives (obtained in an S N2′ reaction of the corresponding primary allylic mesylates with ‘Bu 3SnCu’) decompose at high temperatures with elimination of the stannyl moiety and opening of the sugar ring. The product––a dienoaldehyde with a cis-geometry across the internal double bond––is formed via the anti-( E2)-elimination process as proven by the 117Sn NMR spectroscopy.

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