On the Stereoselectivity of the Synthesis of 1-Hydroxymethyl-4-phenylsulfonylbuta-1,3-dienes from β,γ-Unsaturated Sulfones

Abstract

Starting from D-mannitol, eight β,γ-unsaturated sulfones with different substitution patterns have been synthesised. Reaction of these sulfones with different bases led to 1-hydroxymethyl-4-phenylsulfonylbuta-1,3-dienes with excellent stereocontrol. The stereoselectivity of this reaction is explained and an abbreviated reaction course is proposed that justifies the results obtained.

Key words

sulfone - diene - stereoselectivity - synthesis

References

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7

For compound 1 see also reference 5a.

12

For compounds 10a and 10b see also reference 8.