期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 20, 期 52, 页码 17565-17571出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201404648
关键词
amides; chemoselectivity; nitrogen; nucleophilic addition; sequential reactions
资金
- MEXT [24750045]
- Naito Foundation
- Grants-in-Aid for Scientific Research [24750045] Funding Source: KAKEN
As the complexity of targeted molecules increases in modern organic synthesis, chemoselectivity is recognized as an important factor in the development of new methodologies. Chemoselective nucleophilic addition to amide carbonyl centers is a challenge because classical methods require harsh reaction conditions to overcome the poor electrophilicity of the amide carbonyl group. We have successfully developed a reductive nucleophilic addition of mild nucleophiles to tertiary amides, secondary amides, and N-methoxyamides that uses the Schwartz reagent [Cp2ZrHCl]. The reaction took place in a highly chemoselective fashion in the presence of a variety of sensitive functional groups, such as methyl esters, which conventionally require protection prior to nucleophilic addition. The reaction will be applicable to the concise synthesis of complex natural alkaloids from readily available amide groups.
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