4746-86-5Relevant articles and documents
Rapid, One-Step Synthesis of α-Ketoacetals via Electrophilic Etherification
Paris, Timothy J.,Schwartz, Chris,Sundall, Eric,Willand-Charnley, Rachel
, p. 14797 - 14811 (2021/10/20)
Herein, we report a rapid, one-step synthesis of α-ketoacetals via electrophilic etherification of α-alkoxy enolates and monoperoxyacetals. Methyl, primary, and secondary α-ketoacetals were obtained in 44-63% yields from tetrahydropyranyl substrates; usin
The Acceleration of the Rearrangement of α-Hydroxy Aldimines by Lewis or Bronsted Acids
Zhang, Xin,Dai, Yijing,Wulff, William D.
, p. 2015 - 2018 (2018/09/18)
An efficient method was developed for the synthesis of α-amino ketones from α-hydroxy imines. The reaction occurs through an α-iminol rearrangement involving the migration of a substituent of the carbinol carbon to the imine carbon. The optimal catalysts were found to be silica gel or montmorillonite K 10, which effected migration of a variety of aryl and alkyl substituents in high yields. The rearrangement can also be carried out on imines generated in situ from aldehydes and amines in essentially the same yields as those from the preformed imines.
Catalytic asymmetric α-iminol rearrangement: New chiral platforms
Zhang, Xin,Staples, Richard J.,Rheingold, Arnold L,Wulff, William D.
supporting information, p. 13971 - 13974 (2014/12/10)
A series of 19 different asymmetric catalysts were screened in an effort to identify the first chiral catalyst for the rearrangement of α-hydroxy imines to α-amino ketones involving a 1,2-carbon shift. Although aluminate complexes of VAPOL, VANOL, and 7,7'-tBu2VANOL were quite effective catalysts giving up to 88% ee, the ne plus ultra catalyst for this reaction was found to be a zirconium complex of VANOL which gives 97 to >99% ee for the majority of the substrates examined. An X-ray diffraction study of the catalyst reveals that the zirconium exists as a homoleptic complex with three VANOL ligands and two protonated N-methyl imidazoles.
