Highly Diastereoselective Synthesis of Substituted Epichlorohydrins and Regioselective Preparation of Allyl Alcohols using Chloro or Idomethyllithium

Article abstract of DOI:10.1016/0040-4020(95)90943-Q

Substituted epichlorohydrins 3 or 6 are obtained α-bromo or α-chlorocarbonyl compounds (1 or 4) and chloro or iodomethyllithium, respectively.Starting from α-bromocarbonyl compounds 1 or acyclic α-chloro ketones the reaction takes place with total diastereoselectivity.Treatment of epichlorohydrins 3 or 6 with lithium iodide affords the same substituted allyl alcohols 7 in a regioselective manner.A mechanism to explain this transformation is proposed.Regioisomeric allyl alcohols 11 are prepared by reaction of epichlorohydrins 6 with lithium powder.