Abstract
Reaction of 2-alkyl-4-enamides 2, 9–15 with NIS and aqueous sodium bicarbonate results in the diastereoselective formation of the corresponding iodohydrins 3, 16–22 with essentially no iodolactone by-product. This methodology has been successfully employed for the synthesis of the epoxide intermediate 4 of the orally active Merck HIV-1 protease inhibitor L-735,524.
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