Synthesis of trans olefins by a nickel-catalyzed reduction of enol ethers. A formal, total synthesis of (.+-.)-recifeiolide

JP Ducoux, P Le Menez, N Kunesch…

Index: Ducoux, Jean-Philippe; Menez, Patrick Le; Kunesch, Nicole; Wenkert, Ernest Journal of Organic Chemistry, 1993 , vol. 58, # 5 p. 1290 - 1292

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Citation Number: 21

Abstract

Some time ago it was shown that the interaction of enol ethers with Grignard reagents, catalyzed by low-valent nickel species, led to replacement of the alkoxy groups by alkyl or aryl units, creating olefins with retention of configuratione2 When cyclic enol ethers were used in this reaction, cis olefii were f0rmed, 2c*~*~ a procedure which has been applied to the synthesis of pheromones. 2c. d It now became of interest to utilize the same enol ...

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