Research Progress on Nitroso-ene Reaction

黄莎华,; 霍华兴,; 李文华,; 洪然,

doi:10.6023/cjoc201207026

Chin. J. Org. Chem.

2012

DOI: 10.6023/cjoc201207026

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Research Progress on Nitroso-ene Reaction

黄莎华黄莎华¹,

霍华兴霍华兴²,

李文华李文华³

et al.

Abstract: Nitroso-ene reaction is one of the most efficient methods to construct allylamines which are the versatile building block in synthetic organic chemistry. The reaction has been embedded as the key step in the total synthesis of natural products and pharmaceuticals. This review focuses on the development, application and mechanistic study of nitroso-ene reaction.

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Cited by 11 publications

References 13 publications

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Enantioselective Total Synthesis of (−)‐Hosieine A

Ouyang

Yan

et al. 2015

Angewandte Chemie

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The first total synthesis of (À)-hosieine Aw as accomplished and features an unprecedented nitroso-ene cyclization to construct the 2-azabicyclo[3.2.1]octane ring system. Phosphine-enabled stereoselective bromohydrination provided interesting mechanistic insights into the anti-Markovnikov process.A lso noteworthy is the retention of stereochemistry at C9 in the facile radical debromination initiated by Et 3 B/air.

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Enantioselective Total Synthesis of (−)‐Hosieine A

Ouyang

Yan

et al. 2015

Angewandte Chemie

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Total Synthesis of (+)‐ and (±)‐Hosieine A

2018

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Described herein is ac oncise total synthesis of the highly potent nicotinic acetylcholine receptor ligand hosieine A in racemic and enantioenriched forms.T he synthesis requires only seven steps and features at elescoped reaction sequence initiated by ag old-catalyzed Rautenstrauchreaction.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.Scheme 2. Seven-step synthesis of (AE)-2.D CM = dichloromethane, LDA = lithium diisopropylamide, Tf = trifluoromethanesulfonyl, THF = tetrahydrofuran, TMS = trimethylsilyl.Scheme 3. Gold-catalyzed asymmetric Rautenstrauch reaction. EWG = electron-withdrawing group, Piv = pivaloyl.

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Enantioselective Total Synthesis of (−)‐Hosieine A

Ouyang

Yan

et al. 2015

Angew Chem Int Ed

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The first total synthesis of (-)-hosieine A was accomplished and features an unprecedented nitroso-ene cyclization to construct the 2-azabicyclo[3.2.1]octane ring system. Phosphine-enabled stereoselective bromohydrination provided interesting mechanistic insights into the anti-Markovnikov process. Also noteworthy is the retention of stereochemistry at C9 in the facile radical debromination initiated by Et3 B/air.

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Research Progress on Nitroso-ene Reaction

Cited by 11 publications

References 13 publications

Enantioselective Total Synthesis of (−)‐Hosieine A

Enantioselective Total Synthesis of (−)‐Hosieine A

Total Synthesis of (+)‐ and (±)‐Hosieine A

Enantioselective Total Synthesis of (−)‐Hosieine A

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