An efficient Bi/NH4I-mediated addition reaction for the highly diastereoselective synthesis of homoallylic alcohols in aqueous media

The application of multicomponent reactions has been recognized as the most versatile strategy to achieve molecular diversity in organic synthesis. The reaction pathway and selectivity control of multicomponent reactions are associated with the effectiveness, the economy, and cleanliness of the process. Herein, a copper-catalyzed switchable process for the selective synthesis of N-propargyl oxazolidines and N,N-dipropargyl vicinal amino alcohols, by propargylation of amino alcohols, is disclosed. Mechanistic studies support a sequential process involving a copper-catalyzed annulation/A 3 -coupling of amino alcohol, and copper-catalyzed ring-opening alkynylation of the oxazolidine intermediate. Notably, the iodide anion would not affect the generation of oxazolidines, but it could shut down the cascade procedure of the alkynylation of these oxazolidines.

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Switchable Mono‐ and Dipropargylation of Amino Alcohols: A Unique Property of the Iodide Anion in Controlling Ring‐Opening Alkynylation

Feng

Wang

Cao

et al. 2021

Eur J Org Chem

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Bismuth trichloride-catalyzed oxy-Michael addition of water and alcohol to α,β-unsaturated ketones

Feng

Yun

et al. 2020

Chinese Chemical Letters

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Iron(0)-Mediated Henry-Type Reaction of Bromonitromethane with Aldehydes for the Efficient Synthesis of 2-Nitro-alkan-1-ols

Zhang¹,

Li²,

Li³

et al. 2022

Chinese Journal of Organic Chemistry

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The Henry-type reaction of bromonitromethane with various aldehydes for the efficient synthesis of 2-nitro-alkan-1-ols by using inexpensive and commercial iron powder as reaction mediator was developed. The reaction proceeded efficiently in the presence of PbCl2 and tetrabutylammonium hydrogen sulfate (TBAHS) to produce the desired products in moderate to good yield with wide functional group tolerance.

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An efficient Bi/NH4I-mediated addition reaction for the highly diastereoselective synthesis of homoallylic alcohols in aqueous media

Cited by 3 publications

References 110 publications

Switchable Mono‐ and Dipropargylation of Amino Alcohols: A Unique Property of the Iodide Anion in Controlling Ring‐Opening Alkynylation

Switchable Mono‐ and Dipropargylation of Amino Alcohols: A Unique Property of the Iodide Anion in Controlling Ring‐Opening Alkynylation

Bismuth trichloride-catalyzed oxy-Michael addition of water and alcohol to α,β-unsaturated ketones

Iron(0)-Mediated Henry-Type Reaction of Bromonitromethane with Aldehydes for the Efficient Synthesis of 2-Nitro-alkan-1-ols

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