Design and synthesis of Fmoc-SPPS-ready iodoarene amino acid pre-catalysts and their reactivity in the catalytic oxytosylation of ketones

TETRAHEDRON LETTERS

卷:61

Article

Lex, Timothy R.¹  Swasy, Maria, I¹  Panda, Soham¹  Brummel, Beau R.¹  Giambalvo, Lauren N.¹  Gross, Kristopher G.¹  McMillen, Colin D.¹  Kobra, Khadijatul¹  Pennington, William T.¹  Whitehead, Daniel C.¹ 

[1] Clemson Univ, Dept Chem, Clemson, SC 29634 USA

关键词: Hypervalent iodine;    Oxidation;    Catalysis;    Amino acid;   

DOI  :  10.1016/j.tetlet.2020.151723

来源: Elsevier

【 摘 要 】

A small suite of iodo-aryl amide containing amino acids were synthesized and assessed as catalysts for the hypervalent iodine(III) mediated alpha-oxytosylation of ketones. The efficiency of each catalyst was determined by comparing the relative rates of catalysis in the direct alpha-oxytosylation of propiophenone. In addition, these catalysts can be easily converted to congeners that are suitable for Fmoc-solid phase peptide synthesis for facile incorporation into a chiral peptide framework. This work facilitates the broader goal of our program to develop peptide-based enantioselective catalysts for hypervalent iodine chemistry. (C) 2020 Elsevier Ltd. All rights reserved.

【 授权许可】

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