Abstract
Functionalized gamma-lactams are found to be crucial intermediates in the synthesis of biologically important natural products. We herein described a highly diastereoselective synthesis of beta-carboxy-gamma-lactams and their ethyl ester derivatives, in high yields with high diastereomeric ratio, via the Mukaiyama-aldol type reaction of 2,5-bis(trimethysilyloxy)furan with imines, employing Sc(OTf)(3) as a catalyst.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Carboxylic Acids / chemistry*
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Catalysis
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Esters / chemical synthesis*
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Esters / chemistry
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Ethylenes / chemistry*
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Furans / chemistry*
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Imines / chemistry*
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Lactams / chemical synthesis*
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Lactams / chemistry
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Mesylates / chemistry*
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Molecular Structure
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Scandium / chemistry*
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Stereoisomerism
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Trimethylsilyl Compounds / chemistry*
Substances
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2,5-bis(trimethylsilyloxy)furan
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Carboxylic Acids
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Esters
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Ethylenes
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Furans
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Imines
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Lactams
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Mesylates
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Trimethylsilyl Compounds
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scandium triflate
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ethylene
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Scandium