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Carbanion-accelerated Claisen rearrangements. 8. Phosphonamide anion-stabilizing groups

SE Denmark, H Stadler, RL Dorow…

文献索引:Denmark, Scott E.; Stadler, Heinz; Dorow, Roberta L.; Kim, Jung-Ho Journal of Organic Chemistry, 1991 , vol. 56, # 17 p. 5063 - 5079

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被引用次数: 58

摘要

The utility of various phosphonamide groups has been examined in the context of the carbanion-accelerated Claisen rearrangement (CACR). An extensive survey has identified the NJV'-dibenzyl-l, 3, 2-diazaphospholidine group 11 to be optimal in the ease of construction of the CACR precursors and the facility and stereoselectivity of the rearrangement. Using n-butyllithium as the base, the phosphonamides rearranged readily ...