Please use this identifier to cite or link to this item: http://dx.doi.org/10.18419/opus-6987
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
metadata.ubs.publikation.typ: Zeitschriftenartikel
metadata.ubs.publikation.source: Journal of Organic Chemistry 56 (1991), S. 5883-5889. URL http://dx.doi.org./10.1021/jo00020a033
URI: http://nbn-resolving.de/urn:nbn:de:bsz:93-opus-41697
http://elib.uni-stuttgart.de/handle/11682/7004
http://dx.doi.org/10.18419/opus-6987
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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