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Please login to access the full content or check if you have access via Method 9: Prévost–Woodward Dihydroxylation

DOI: 10.1055/sos-SD-036-00589

Nativi, C.; Roelens, S.Science of Synthesis, (200836773.

The reaction of alkenes with iodine and silver acetate in aqueous acetic acid (Woodward's dihydroxylation) is characterized by syn dihydroxylation of the more hindered face of the alkene.[‌84‌] Conversely, anti dihydroxylation is generally achieved using iodine and silver benzoate in the absence of water, following Prévost's procedure.[‌85‌] This is exemplified by the conversion of styrene into 1,2-dibenzoate 55, which is then saponified to the corresponding anti-1,2-diol (Scheme 25).[‌86‌]

Meeeee 88 Meeeeeeeeeeeeee ee Meeeeee eeeee Meéeeee Meeeeeeeee[‌88‌,‌88‌]

Me eee Meéeeee eeeeeeee, eee eeeeeee eeee 88 (M8=Me) (eeeeeee eeee eeee eeeee 88) eeeeeeeee eeeeeeeeeeee eeee eeeeeee eeee eeeeeeee eeeee ee eeee eee eeee-eeeeeeeeee 88 (Meeeee 88). Mee eeeeeeee ee eeeee eeeeeee eee eeeeee ee eee eeeeeeee; eeeee eeeeeee ee eee eeeeeee ee eee eeeeeeeee eeeeeeee eeeeee eeee ee eee eeeeeeeee eeeeeeeeeeee 88 (M8=Me). Mee eeeeeeeee eeeeee eeeeeeeeeeee 88 ee eeee eeeeeee ee e eeeeeeeeeeee eee-eeee 88. Mee eeeeeee eeee eee ee eeeeeeee ee eeeeeeeeee eeeeeeeeee. Meeeeeee eeeee eeee eeee eeeeeeeeeeee ee eee Meéeeee eeeeeeee eee ee eeee ee eeeeeee eee eeeeeeee eeeeee eeeeeeeeeee ee eeee eeeeeeee ee eee eeeeeeeee ee eeeeeee eeee eeeeee(MMMM) eeeee.[‌88‌]

Meeeee 88 Meeeeeee Meeeeeeeeeee ee eee Meéeeee Meeeeeee[‌88‌]

Meee eee eee ee eeeeeeee eee eee ee eeeeeeeee eeeeee eeeee eee eee eeeeeeeee ee eeeee eeeeeee ee eeeeeee eee eeeeeeeee eeeeee, e eeeeeee ee eee eeeeeeee eee eeeeeeeee eeeeeeeee eeeeeeeeeeeeee eeeeeee ee eeeeeeeee eeeeeee, eeee ee, e eeeeeeeeee-eeeee-eeee eeeeeee ee eee MeéeeeeMeeeeeee eeeeeeee.[‌88‌] 8,8-Meee 88 eee ee eeeeeeee eeee eeeeeee (88) eeeee e eeeeeeeee eeeeee ee eeeeeee eeeeeee (88eee%) eee eeeeee eeeeeeeee (88eee%) ee eeeeee eeee ee 88°M ee eeee e eeeeeee ee eee eeeeeeeeeeeee eeeeeee eeeeeeeeeeee 88 eee 88 eee eee eeeeeeeee 88 ee 88% eeeeeee eeeee. Meeeeeeeee eeeeeeeeee ee eeee eeeeeee eeeeeee ee eee eeeeeeeee ee 8-eeeeeeeeeeee-8,8-eeee (88) ee 88% eeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeee-Meee Meeeeeeeeeeeeee ee Meeeeee[‌88‌]

Meeeeeeee, eeeeeeee, eeeeeee, eeeeeeeeeeeee, eee α,β-eeeeeeeeeee eeeeeee, eeee eeeeeeee-eeeeeeee eee eeeeeeee-eeeeeeeeeee eeeeee, eeeeeee eeeeeeeeeeeeeee ee eeeeeee eee eeeeeeeeeeeee eeeee ee eeeeeeeee eeeee eeee eeee eeeeeeeeeeeeeeeeeeee: eee eee eee eeee eeeeeeeeeee ee eeee eeeeeeeeee ee eeeee eee eeee, ee eee eeeeee ee Meéeeee ee Meeeeeee eeeeeeeeee. eeee-Meeee eee eeeeeeee eeee (eeeeeeeeeeeee)eeeeeee ee eeeeeeee ee eee eeeeeee ee eeeeeeeeeeeeee eeeeeee eeeee eee eeee eeeeeeee eeeeeeeeee.

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeee-8,8-eeee (88); Meeeeee Meeeeeeee:[‌88‌]

Meeeeee MeMM (8eM) eee eeeee ee e eeeeeee ee eeeeeee (88; 888ee, 8eeee), MeMM8 (888ee, 8.8eeee), eee MeMe (88ee, 8.8eeee) ee e 88-eM eeeee-eeeeeeee eeeee. Mee eeeeeee eee eeeeee ee 88°M eee 88e. Mee eeeee-eeeeee eeeeeee eeeeee eeeeee eeeee eeeeeeeeee ee eee eeeeeeee. Mee eeeeeee eee eeee eeeeee eee eeeeeeeee eeee MeMMe (8×88eM). Mee eeeeeeee eeeeeee eeeeeeeee eeee eeeeee eeee eee. ee Me8M8M8, M8M, eee ee MeMMM8. Mee eeeeeee eeeee eee eeeee (Me8MM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. M eeeeeee ee eee eeeeeee, M8MM8 (888ee, 8.8eeee), eee MeMM (88eM) eee eeeeeee ee 88°M eee 88e. Mee MeMM eee eeee eeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeeeeee eeee MeMMe (8 × 88eM). Mee eeeeeeee eeeeeee eeeee eee eeeeee eeee M8M eee eeeee. Mee eeeeeee eeeee eee eeeee eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee); eeeee: 888ee (88%).