Iminoiodane mediated aziridination of α-allylglycine:: access to a novel rigid arginine derivative and to the natural amino acid enduracididine

The synthesis of fully protected ammodihydrohistidines in optically pure form is described starting from allylglycine derivatives. These compounds represent novel conformationally constrained analogues of arginine, one of them being, in addition, a protected form of the marine natural product, enduracididine. The key step of the strategy is a one-pot copper-catalyzed aziridination of t-butyl (S)-N-(9-phenyl-9H-fluoren-9-yl)allylglycinate ((S)-16) with 2-trimethylsilylethanesulfonamide in the presence of iodosylbenzene. (C) 2004 Published by Elsevier Ltd.