Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 349, Issue 3, Pages 417-424Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200600370
Keywords
carbohydrate scaffolds; enantioselective; organic catalysis; glucosamine derivatives; Mannich reaction; Strecker reaction
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Efficient organocatalysts for enantioselective Strecker and Mannich reactions were constructed from glucosamine as a readily accessible chiral scaffold. A variety of aromatic aldimines were subjected to hydrocyanation with good to excellent yield (72-98 %) and, in part, high enantioselectivity (69-95 % ee). Influence of the catalyst architecture on the enantioselectivity obviously arises from restrictions imposed on the conformational flexibility of the monosaccharidic backbone. In the asymmetric Mannich reaction moderate yields (up to 76 %) and enantioselectivities (up to 58 % ee) have been achieved with the described catalyst.
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