Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest. Please login or sign up for a free trial to access the full content.
26.1.3.3.3.1.2 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).

Me eeeeeeeeeeee eeeeeee, eeeeeee eeeeeeeeeeeeeeeee (8 eeeee), eeeeeeee ee eeeeeeee eeee eeeeeeeeeee, eee ee eeee eee eee eeeeeeeeeeeee ee eeeeeee-eeee eeeeeeeee eee eeeeeeeee, eeeeee, eee eeeeeeeeeeeeee eeeeeee ee eeee eeeeeee 88 (Meeeee 88).[‌888‌] Meeeeee eeeeeeeeeeeee ee eee eeeeeee eeeee eeeeeeee ee eeeeeeee ee eee eeeeee eeeeeeeeee ee eeeeeee eeeeeeeeeeeeeeeee ee eee eeeeeeee eeeee eee eeeeeeeeeee ee eee eeeeeeeeee eeee eeee eeeeee eeeeee, eeeee eee eeeeeeeeeeeee eeeeeeeeeee eeee. Meeeeeeeee eeeeeeeeeee ee eeeeeeeeeeeeeeeeeeeeeee eeeee eeeeeee eeeeeeee Meeeee-eeee eeeeeeeeeeeee eee eeeee eeeeeeeeeee ee eee eeeeeeeeeeeee eeeeeee eeee eeeeee eeee eeeee eee eeeee eeeeee.

Meeeee 88 Meeeeeeee ee α-Meeeeee Meeeeee eeee Meeeeeeee Meee,[‌888‌] Meeeeeeeee/Meeeee,[‌888‌] ee Meeeeee Meeeeeeeeeeeeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 M8 Meeee Mee
Me Me M 88 [‌888‌]
8-MeMM8M8 8-MeMM8M8 M 88 [‌888‌]
Me Me Me 88 [‌888‌]
(MM8)88 M 88 [‌888‌]
Me Me M 88 [‌888‌]
8-eeeee 8-eeeee M 88 [‌888‌]

Meeeeeeeeeee Meeeeeeee

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

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

Meeeeeeeeeeeeeeeeee eeeeeeee (8.8e, 88.8eeee) eee eeeee eeeeeeee ee e eeeeeeeeee ee Me eeee (888ee, 88.8eeee) ee MMM (88eM) ee ee. Meeee eeeee 8e eeee ee eee Me eee eeeeeeeee, eee eeeeee MeMMe8 eee eeeeeeeee eeee eee eeeeeeeee Me, eee e eeee ee eeeeeee (8.8e, 88.8eeee) ee MMM (88eM) eee eeeee eeeeeeee. Mee eeeee eeeeee eeeeeee eee eeeeeee eeeeeeeee ee ee eee MeMM (888ee, 88.8eeee) eee eeeee, eeeeeeee ee MeM (8.8e, 88.8eeee). Meeee eeeeeeee eee ee eeeeeeeeee 88eee, eee eeeeeee eee eeeeee eeee M8M (888eM) eee eeeeeeeee eeee MeMMe. Mee eeeeeeee eeeeeee eeeeeeee eeee eeeee (MeMM8) eee eeeeeeeeeeee ee eeeee eeeeee e eeeeee eee. MMMM eeeeeeeeeeee ee eeeeee eee (MeMMe) eeee 88 (M8=M8=Me; M8=M); eeeee: 8.8e (88%); ee 8888°M.

References