Tetrahedron

Highly diastereoselective synthesis of substituted epichlorohydrins and regioselective preparation of allyl alcohols using chloro or iodomethyllithium

JM Concellón, L Llavona, PL Bernad

文献索引：Concellon, Jose M.; Llavona, Lujan; Bernad, Pablo L. Jr. Tetrahedron, 1995 , vol. 51, # 19 p. 5573 - 5584

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被引用次数: 17

摘要

Substituted epichlorohydrins 3 or 6 are obtained from 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 ...