Science of Synthesis

Yus, M.; Nájera, C., Science of Synthesis, (2005) 26, 178.

Hydriodic acid in acetic acid or chloroform[‌247‌–‌249‌] 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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‌Meeeee 88‌ Meeeeeeee ee α-Meeeeee Meeeeee eeee Meeeeeeee Meee,[‌888‌] Meeeeeeeee/Meeeee,[‌888‌] ee Meeeeee Meeeeeeeeeeeeeeee[‌888‌]

‌Meeeeeeeeee 88‌

Meeeeeeeeeee Meeeeeeee

8e-Meeeee-8-eeeeeeeeeeeeee-8M-eeeee-8-eee (‌88‌):[‌888‌]

Mee eeeeeee eeeeee (88.8 ee, 8.888 eeee) eee eeeeeeeee ee MeMM (8 eM) eee 88% MM (8.8 eM) eee eeeee. Mee eeeeeeeee eeeee eeee eee eeeeeeee eee 88 eee eee eeeee eeeeeee ee ee, eee eeeeee eeee ee eee-eeeeee eeeeeee ee MeMMM8 (8.8 e) eee 8 M ee MeMM (8 eM). Mee eeeeeeeee eeee eee eeeeeeeee eeee Me8M (8 × 88 eM) eee eee eeeeeeee eeeeeeee eeee eeeeee eeeeeeeeeeee eeee ee MeMMM8 (8 × 88 eM) eee eeeee (88 eM), eee eeee eeeee (MeMM8). Mee eeeeeee eee eeeeeee eeeee eeeeee ee eeee e eeeeeee ee eeeeeeeeeeeeee ‌88‌, eeeee eeee eeeeeeee ee MMMM ee eeeeee eee eee-eee eeeee-eeeeeee; eeeee: 88.8 ee (88%) eee 8.8 ee (88%), eeeeeeeeeeee.

Meeeee Meeeee Meeeee (‌88‌, M8 = M8 = Me; M8 = M); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeeeee, eeeeeeeee, ee eeeeeeeeee ee eeeeeeeeeee eeeeeee eee eeee eee ee eeeee.

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References

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• 8.Meeeee-Meee, (8888) 8/8e, 8888.