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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…

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

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被引用次数: 37

摘要

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- ...