Chemoselective Reductive Nucleophilic Addition to Tertiary Amides,Secondary Amides,and N‐Methoxyamides |
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| Authors: | Minami Nakajima Yukiko Oda Takamasa Wada Ryo Minamikawa Dr Kenji Shirokane Dr Takaaki Sato Noritaka Chida |
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| Affiliation: | Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3‐14‐1, Hiyoshi, Kohoku‐ku, Yokohama 223‐8522 (Japan), Fax: (+81)?45‐566‐1551 |
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| Abstract: | 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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| Keywords: | amides chemoselectivity nitrogen nucleophilic addition sequential reactions |
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