Practical Peptide Synthesis Mediated by a Recyclable
Hypervalent Iodine Reagent and Tris(4-methoxyphenyl)phosphine
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Abstract
6-(3,5-Bis(trifluoromethyl)phenyl)-1<i>H</i>,4<i>H</i>-2aλ<sup>3</sup>-ioda-2,3-dioxacyclopenta[<i>hi</i>]indene-1,4-dione (<i>p</i>-BTFP-iodosodilactone, <b>1a</b>) was synthesized and demonstrated to be an efficient hypervalent
iodine(III) reagent for the synthesis of dipeptides from various standard
amino acids, including sterically hindered amino acids, in good to
high yields within 30 min in the presence of tris(4-methoxyphenyl)phosphine.
In addition, the combined system of <b>1a/</b>(4-MeOC<sub>6</sub>H<sub>4</sub>)<sub>3</sub>P was used to synthesize the pentapeptide
leu-enkephalin in protected form. It is worth noting that <b>1a</b> can be regenerated readily after reaction
