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A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
A Direct Route to Deuterated gem-Difluorinated Cyclopropanes via Base-Catalyzed H/D Exchange
Le Zhang1, Xu Wang2, Liping Zhao2
1West China School of Public Health and West China Fourth Hospital, and State Key Laboratory of Biotherapy, Sichuan University, Chengdu 610041, China.
Abstract:
Deuterated compounds are significantly important in multiple domains. Herein, we report a mild and efficient method to synthesize deuterated gem-difluorinated cyclopropanes via base-catalyzed H/D exchange with an excellent level of deuterium incorporation. This approach was mediated by a catalytic amount of sodium tert-butoxide or potassium tert-butoxide with DMSO-d6 as the deuterium source. Mechanistic studies indicate that this reaction proceeds via an anionic pathway. The scale-up synthesis and the preserved deuterium incorporation in downstream transformations demonstrate the practical applicability of this method.
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