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Stereoselective Syntheses of Chiral Heterocycles and Alkaloids Using Carbohydrate Auxiliaries

Kunz H., Weymann M., Follmann M.

Polish Journal of Chemistry

1999

vol. 73 nr 1

15-27

N-Glycosyl imines show an efficient diastereofacial differentiation in their reactions with nucleophiles. Coordination to suitable Lewis acids enhances this effect, which is demonstrated in thee nantioselective syntheses of a-amino acids, homoallylamines and b-amino acids. Asymmetric aza Diels-Alder and tandem Mannich-Michael reactions have been applied for the enantioselective synthesis of chiral piperidine derivatives including alkaloids, e.g. anabasin, gephyrotoxin 167 B, pumiliotoxin C and its 4a-epimer.