Tetrahedron

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

L Sanière, L Leman, JJ Bourguignon, P Dauban…

Index: Saniere, Laurent; Leman, Loic; Bourguignon, Jean-Jacques; Dauban, Philippe; Dodd, Robert H. Tetrahedron, 2004 , vol. 60, # 28 p. 5889 - 5897

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Citation Number: 37

Abstract

The synthesis of fully protected aminodihydrohistidines 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 () with 2- ...