Journal
ORGANIC LETTERS
Volume 24, Issue 4, Pages 1105-1109Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c00084
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Funding
- JSPS KAKENHI [JP19H00895]
- JST CREST Grant [JPMJCR19R4]
- Asahi Glass Foundation
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In this study, treatment of arylcyclopropanecarboxamides with a sodium dispersion in the presence of methoxypinacolborane as a reduction-resistant electrophile was investigated. The results showed that the reaction led to the reductive cleavage of the cyclopropane ring followed by instant trapping with the boron electrophile, resulting in the formation of enolates of gamma-aryl-gamma-borylalkanamides. The enolates could further react with a different electrophile to produce the corresponding a-substituted amides with anti selectivity.
Treatment of arylcyclopropanecarboxamides with a sodium dispersion in the presence of methoxypinacolborane as a reduction-resistant electrophile leads to reductive cleavage of the cyclopropane ring followed by instant trapping with the boron electrophile to yield the enolates of gamma-aryl-gamma-borylalkanamides. The enolates react further with a different electrophile to yield the corresponding a-substituted amides with anti selectivity.
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