The Journal of Organic Chemistry

Carbohydrates as chiral templates: diastereoselective synthesis of N-glycosyl-N-homoallylamines and. beta.-amino acids from imines

S Laschat, H Kunz

Index: Laschat, Sabine; Kunz, Horst Journal of Organic Chemistry, 1991 , vol. 56, # 20 p. 5883 - 5889

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Citation Number: 125

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 SnCh, imines 2 of aromatic and heteroaromatic aldehydes were converted to homdylamines 3, giving ratios of diastereomers higher than 7: l. No addition products derived from a-anomeric aromatic imines were formed. Aliphatic ...