0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via Variation 6: Addition of Allylic Indium Reagents

DOI: 10.1055/sos-SD-036-00193

Frost, C. G.; Le Nôtre, J.Science of Synthesis, (200836327.

The first example of a Barbier-type addition of allyl halides to carbonyl compounds mediated by indium was reported in 1988.[‌360‌] Since then a wide variety of allylic substrates gave been utilized in the addition of allylic indium reagents to aldehydes and ketones.[‌361‌‌365‌] An unusual feature of the addition of allylic indium reagents is that the reactions are preferably performed in water or water-containing solvents. This is illustrated in the stereoselective indium-promoted allylations of β-hydroxy aldehydes in water.[‌366‌] The free hydroxy derivatives react with excellent diastereofacial control to afford anti-1,3-diols such as 121A (Scheme 68).

Meeeee 88 Mee Meeeeeeeeeeeeee Meeeeeee ee ee Meeeeeeeeee Meeeeee ee e β-Meeeeee Meeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeeeeee Meeeeeee, e.e. 888; Meeeeee Meeeeeeee:[‌888‌]

M eeeeeeeeeeee eeeeeee eeee ee eee eeeeeeee (8.888eeee) ee M8M (8.8eM) eee eeeeeee eeee Me eeeeee (888ee, 8.888eeee) eee eeeee eeeeeee (888ee, 8.88eeee). Mee eeeeeeee eee eeeeeee ee eeeeeee eeeee ee eeeeeeee eeeeeeee eeeeeeee (MMM eeeeeeee). MeMMe eee eeeee, eeeeeeee eee eeeeeeeeee eee 88eee, eee eee eeeeeeeee eeeeeee eeeee eee eeeeeeeee eeee MeMMe. Mee eeeeeeee eeeeeee eeeeee eeee eeeee eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/MeMMe 88:8).