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We demonstrate the utility of carbenylative aminations in the synthesis of the cyclic alkaloid nitensidine E involving both protected and un-protected guanidine moieties. The alkylguanidine substrate is generated using a Mitsunobu reaction and we show that NH chemical shifts correlate with the regiochemistry and tautomeric structure of N-alkyl-bis-N,N′-Boc-guanidines. When the doubly-protected guanidine...
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