Development of Efficient Synthetic Reactions Using Enamines and Enamides Carrying Oxygen Atom Substituent on Nitrogen Atom

Miyata, Okiko

doi:10.1248/cpb.c23-00915

CHEMICAL & PHARMACEUTICAL BULLETIN

2024

DOI: 10.1248/cpb.c23-00915

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Development of Efficient Synthetic Reactions Using Enamines and Enamides Carrying Oxygen Atom Substituent on Nitrogen Atom

Okiko Miyata

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2024

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Umpolung Approach to Aldol Products via Isoxazoline N-Oxides as Intermediates

Ushakov,

Sukhorukov

2024

J. Org. Chem.

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A two-step umpolung approach to the diastereoselective synthesis of aldols was developed, in which a conjugated nitroalkene is used as the synthetic equivalent of the enolonium cation, while a sulfur ylide acts as the equivalent of the α-carbinol anion. The resulting isoxazoline N-oxides undergo catalytic reductive cleavage to aldols under mild conditions at room temperature and under 1 atm hydrogen pressure. The efficiency of the method was demonstrated by the synthesis of a series of polysubstituted β-hydroxyketones that are difficult to synthesize using the classical aldol reaction. The developed approach allows for the regiodivergent assembly of aldols by selecting a nitroalkene isomer with the appropriate position of the C,C double bond.

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Umpolung Approach to Aldol Products via Isoxazoline N-Oxides as Intermediates

Ushakov,

Sukhorukov

2024

J. Org. Chem.

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show abstract

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Development of Efficient Synthetic Reactions Using Enamines and Enamides Carrying Oxygen Atom Substituent on Nitrogen Atom

Cited by 1 publication

References 168 publications

Umpolung Approach to Aldol Products via Isoxazoline N-Oxides as Intermediates

Umpolung Approach to Aldol Products via Isoxazoline N-Oxides as Intermediates

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