56535-63-8Relevant articles and documents
A facile access to pyrroles from amino acids via an aza-Wacker cyclization
Zhang, Zuhui,Zhang, Jintang,Tan, Jiajing,Wang, Zhiyong
, p. 5180 - 5182 (2008/12/20)
(Chemical Equation Presented) A facile and efficient synthesis of pyrroles from readily available amino acids is described. The key step in the method is an aza-Wacker oxidative cyclization catalyzed by palladium(II)/Cu(OTf) 2. A series of pyrroles were obtained by this method under mild conditions.
Acyclic Stereocontrol through the Thio-Claisen Rearrangement of Precursors bearing a Chiral Centre adjacent to Carbon 1
Desert, Stephane,Metzner, Patrick,Ramdani, Mohamed
, p. 10315 - 10326 (2007/10/02)
The Claisen rearrangement of precursors bearing a stereogenic centre adjacent to carbon 1 of the pericyclic nucleus has been investigated in the sulfur series.Dithioesters having a methyl and various alkyl or alkenyls groups on the β-carbon were deprotonated by LDA.The resulting enethiolates were allylated on sulfur to give S-allyl ketenedithioacetals.The thio-Claisen transposition of the latter compounds was achieved either at room temperature or at 101 deg C to afford good yield of allylated dithioesters.Diastereomeric selectivities up to 95:5 have been observed.These results have been explained by a steric effect and correlated to allylic strain values.