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Authors: Laschat, Sabine
Kunz, Horst
Title: Carbohydrates as chiral templates : diastereoselective synthesis of N-glycosyl-N-homoallylamines and β-amino acids from imines
Issue Date: 1991 Zeitschriftenartikel Journal of Organic Chemistry 56 (1991), S. 5883-5889. URL
Abstract: Complexing properties and chirality of carbohydrates were utilized in diastereoselective reactions of 0-pivaloylated N-galactosylimines with allylsilanes and -stannaries. With dyltrimethylsilane in the presence of SnCl4, imines 2 of aromatic and heteroaromatic aldehydes were converted to homdylamines 3, giving ratios of diastereomers higher than 7:1. No addition products derived from α-anomeric aromatic imines were formed. Aliphatic homdylamines 3 were synthesized by using allyltributylstannane 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.
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