137050-87-4Relevant articles and documents
Carbohydrates as Chiral Templates: Diastereoselective Synthesis of N-Glycosyl-N-homoallylamines and and β-Amino Acids from Imines
Laschat, Sabine,Kunz, Horst
, p. 5883 - 5889 (2007/10/02)
Complexing properties and chirality of carbohydrates were utilized in diastereoselective reactions of O-pivaloylated N-galactosylimines with allylsilanes and -stannanes.With allyltrimethylsilane in the presence of SnCl4 imines 2 of aromatic and heteroaromatic aldehydes were converted to homoallylamines 3, giving ratios of diastereomers higher than 7:1.No addition products derived from α-anomeric aromatic imines were formed.Aliphatic homoallylamines 3 were synthesized by using allyltributylatannane in the presence of SnCl4.Both α- and β-anomeric aliphatic imines reacted with the allylstannane.They gave the same ratio of diastereomers and showed the same sense of asymmetric induction.