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Please login or sign up for a free trial to access the full content. Variation 2: Nucleophilic Reagents

DOI: 10.1055/sos-SD-026-00085

Yus, M.; Nájera, C.Science of Synthesis, (200526178.

Hydriodic acid in acetic acid or chloroform[‌247‌‌249‌] is an effective reagent for the reduction of α-hydroxy ketones derived from steroids[‌247‌,‌248‌] and hydroindanones.[‌249‌] Hydroindanone 64 is obtained as a mixture of cis/trans bicyclic ketones (2.4:1) from the α-hydroxy ketone by reduction with hydriodic acid in acetic acid (Scheme 16).[‌249‌] Iodotrimethylsilane reduces secondary hydroxy ketones at room temperature in good yields by formation of the corresponding silyl enol ethers.[‌251‌] The combination of red phosphorus and iodine allows the reduction of benzoins at room temperature in good yield by generation of intermediate α-iodo ketones, which are then reduced by the iodide ion[‌255‌] (Scheme 16).

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