期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 349, 期 3, 页码 417-424出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200600370
关键词
carbohydrate scaffolds; enantioselective; organic catalysis; glucosamine derivatives; Mannich reaction; Strecker reaction
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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