The Journal of organic chemistry

Chemoselective intramolecular alkylation of the blaise reaction intermediates: tandem one-pot synthesis of exo-cyclic enaminoesters and their applications toward the …

JH Kim, H Shin, S Lee

Index: Kim, Ju Hyun; Shin, Hyunik; Lee, Sang-Gi Journal of Organic Chemistry, 2012 , vol. 77, # 3 p. 1560 - 1565

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Citation Number: 21

Abstract

The intramolecular alkylative reactivity and N/C selectivity of the various Blaise reaction intermediates, which are formed from the reaction of the Reformatsky reagents with ω- chloroalkyl nitriles, did not reach the synthetic potential as an entry to exo-cyclic enaminoesters. To circumvent this issue, various additives were investigated, among which the addition of NaHMDS dramatically enhanced the reactivity and N/C selectivity. This ...