141694-63-5Relevant articles and documents
Copper-catalyzed cross-coupling of amino acid-derived amides with (Z)-vinyl iodides: Unexpected solvent effect and preparation of plocabulin
Wang, Leiming,Lei, Xinsheng,Wang, Quanrui,Li, Yingxia
, (2021/02/01)
A copper-catalyzed cross-coupling reaction of amino acid-derived amides and (Z)-vinyl iodide was studied to improve a key step in the synthesis of plocabulin, a novel microtubule destabilizer agent of marine origin. The study revealed a profound solvent effect with 1,2-dimethoxyethane (DME), which gave consistently high yields across a large variety of the amide and (Z)-vinyl iodide substrates. The protocol was successfully utilized in the preparation of plocabulin and provided a significantly improved yield.
Sterically biased 3,3-sigmatropic rearrangement of azides: Efficient preparation of nonracemic α-amino acids and heterocycles
Gagnon, David,Lauzon, Sophie,Godbout, Cedrickx,Spino, Claude
, p. 4769 - 4771 (2007/10/03)
(Chemical Equation Presented) Homochiral α-amino acids, heterocycles, and carbocycles are efficiently constructed via a short sequence of reactions starting from the chiral auxiliary p-menthane-3-carboxaldehyde. The key feature of the sequence is a highly selective tandem Mitsunobu/3,3-sigmatropic rearrangement of hydrazoic acid that procures enantiomerically enriched allylic azides. The sequence is either terminated by oxidative cleavage to provide amino acids or by ring-closing metathesis to provide heterocycles or carbocycles bearing nitrogen.
A new Procedure for the Synthesis of (E)-1-iodo-1-alkenes
Martinez, A. Garcia,Alvarez, R. Martinez,Gonzalez, S. Martinez,Subramanian, L. R.,Conrad, M.
, p. 2043 - 2044 (2007/10/02)
(E)-1-iodo-1-alkenes 4 can be prepared stereoselectively from aldehydes 1 via IH-elimination of 1,1-di-iodoalkanes 3 with DBU. Key words: Vinyl iodide; diiodoalkane; elimination; stereoselectivity.