135866-16-9

Upstream product

• 121732-95-4 N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)benzylideneamine 
• 762-72-1 allyl-trimethyl-silane 
• 24850-33-7 allyltributylstanane 

Relevant academic research and scientific papers

Stereoselective synthesis of 2-substituted pyrrolidines

Using O-pivaloyl protected D-galactopyranosylamine and D-arabinopyranosylamine, (S) or (R) configured α-substituted homoallylamines are synthesized with high diastereoselectivity by reaction of the corresponding aldimines with allyltributylstannane. Electrophile-induced endo-trig-cyclization of these N-glycosylhomoallylamines gave the 2-substituted pyrrolidines of high diastereomeric purity.

Carbohydrates as Chiral Templates: Diastereoselective Synthesis of N-Glycosyl-N-homoallylamines and and β-Amino Acids from Imines

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.