812665-19-3Relevant academic research and scientific papers
A new approach to vinyl glycine derivatives from (+)-(RS)-3-[(p- toluenesulfinyl)methyl]-1-oxa-4-azaspiro[4,5]decen-3-ene
Acherki, Hassan,Alvarez-Ibarra, Carlos,Garcia-Navazo, Gonzalo,Gomez-Sanchez, Elena,Quiroga-Feijoo, Maria L.
, p. 3419 - 3426 (2004)
The diastereoselective reduction of α-benzyl-α-sulfinylketimine 1a with DIBAL-H/ZnCl2, LiEt3BH, and NaCNBH 3/AcOH-TFA has been studied. Under the first conditions, the reaction was completely stereoselective and the sulfinyl group involving the formation of a chelated complex with the metallic ion became the sole chiral controller, regardless of the presence of the α-stereocentre. The title compound 6-I was derivatized as cyclic carbamate 2 and the base induced desulfinylation of this compound allowed the synthesis of the enantiomerically pure N,O-protected N-cyclohexyl-1,2-amino alcohol 3 with total regio- and stereocontrol.
