Tetrahedron p. 5573 - 5584 (1995)
Update date:2022-08-10
Topics:
Concellon, Jose M.
Llavona, Lujan
Bernad, Pablo L. Jr.
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.
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