Abstract
At low temperature and in the presence of an acid catalyst, sulfur
dioxide undergoes hetero-Diels-Alder additions with 1-oxy-1,3-dienes,
giving unstable sultines, which are ionized into zwitterionic species
and react as 1-oxyallylic cation intermediates (Umpolung with SO2 )
with electron-rich alkenes such as allylsilanes or enoxysilanes.
The β,γ-unsaturated silyl sulfinates so-obtained
can be desulfinylated in situ to generate polyketide fragments containing
up to three contiguous stereogenic centers in one-pot operations.
This reaction cascade can be applied in two-directional chain elongation
approaches for the asymmetric synthesis of long chain polyketide
fragments using 1-[(S )- or (R )-1-phenylethoxy]-1,3-dienes.
Key words
hetero-Diels-Alder of sulfur dioxide - asymmetric
synthesis of polyketides - reaction cascade - allylic
cation - allylsilane - enoxysilane
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