1172596-82-5Relevant articles and documents
Dramatic Acceleration of an Acyl Transfer-Initiated Cascade by Using Electron-Rich Amidine-Based Catalysts
Ahlemeyer, Nicholas A.,Streff, Emma V.,Muthupandi, Pandi,Birman, Vladimir B.
, p. 6486 - 6489 (2017)
A tandem rearrangement of α,β-unsaturated thioesters into tricyclic ene-lactones fails with conventional amidine-based catalysts, but becomes possible when their electron-rich analogs are employed. A highly diastereo- and enantioselective version of this process has been developed using H-PIP 1b, a chiral catalyst prepared over a decade ago, but never utilized since its disclosure.
N-urethane-protected amino alkyl isothiocyanates: Synthesis, isolation, characterization, and application to the synthesis of thioureidopeptides
Sureshbabu, Vommina V.,Naik, Shankar A.,Hemantha,Narendra,Das, Ushati,Guru Row, Tayur N.
supporting information; experimental part, p. 5260 - 5266 (2009/12/06)
(Chemical Equation Presented) Synthetically useful N-Fmoc amino-alkyl isothiocyanates have been described, starting from protected amino acids. These compounds have been synthesized in excellent yields by thiocarbonylation of the monoprotected 1,2-diamines with CS2/TEA/p-TsCl, isolated as stable solids, and completely characterized. The procedure has been extended to the synthesis of amino alkyl isothiocyanates from Boc- and Z-protected amino acids as well. The utility of these isothiocyanates for peptidomimetics synthesis has been demonstrated by employing them in the preparation of a series of dithioureidopeptide esters. Boc-Gly-OH and Boc-Phe-OH derived isothiocyanates 9a and 9c have been obtained as single crystals and their structures solved through X-ray diffraction. They belong to the orthorhombic crystal system, and have a single molecule in the asymmetric unit (Z′ = 1). 9a crystallizes in the centrosymmetric space group Pbca, while 9c crystallizes in the noncentrosymmetric space group P212121.
