Abstract
Easily available, six-membered cyclic nitroso acetals 2 are smoothly oxidized with meta-chloroperbenzoic acid to δ-nitro alcohols 3 or γ-nitro carbonyl compounds 4 with the retention of their relative configurations of stereocenters (diastereomeric ratio > 10:1). The reaction sequence – the generation of diastereomerically pure six-membered cyclic nitronates 1 from simple aliphatic nitro compounds (AN), C–C coupling of 1 with π-nucleophiles, and the oxidation of the resulting nitroso acetals 2 – is considered to be a new effective variant of the umpolung reactivity of AN. An original approach for the synthesis of alternative diastereomers of nitro derivatives 3 has also been suggested.
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