Substituent effects in the aliphatic Claisen rearrangement of substituted (1-methyl-3-oxahexa-1, 5-dienyl) amines: synthesis of substituted 2-aminopent-4-enals. …

J Barluenga, F Aznar, R Liz…

文献索引：Barluenga, Jose; Aznar, Fernando; Liz, Ramon; Bayod, Miguel Journal of Organic Chemistry, 1987 , vol. 52, # 23 p. 5190 - 5194

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被引用次数: 16

摘要

The series of substituted@-allyloxy enamines 4 was allowed to undergo Claisen rearrangement. The reaction proved to be faster for enamines derived from aliphatic than those from aromatic amines, the general substituent effects fitting Gajewski's oxaallyl-allyl radical model for these processes. The high stereoselectivity observed in these reactions leading to the 2-aminopent-Cenals 5 was assumed to occur via the more stable chairlike ...