Secondary Phosphine Sulfide‐Enabled Iridium‐Catalyzed Asymmetric Allylic Substitution

Wu, Zeng-Hua; Wang, Huaiyu; Yang, Huai-Lan; Wei, Li-Hua; Hayashi, Tamio; Weng, Duan

doi:10.1002/anie.202213904

Cited by 9 publications

(1 citation statement)

References 92 publications

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“…Secondary phosphine oxides (SPOs) are stable and low-toxicity organophosphorus reagents, which play an important role in the construction of C–P bonds. − In recent years, cyclizations and cycloadditions of SPOs have become useful strategies for the synthesis of structurally diverse phosphorus-containing benzo five-membered heterocycles (Scheme ). − Among these reactions, intramolecular cyclizations , and intermolecular (3 + 2) cycloadditions of SPOs , have been well established (Scheme a,b).…”

Section: Introductionmentioning

confidence: 99%

Organocatalytic Diastereoselective (4 + 1) Cycloaddition of o-Hydroxyphenyl-Substituted Secondary Phosphine Oxides

Wu,

Zhang,

Wang

et al. 2023

J. Org. Chem.

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Section: Introductionmentioning

confidence: 99%

Organocatalytic Diastereoselective (4 + 1) Cycloaddition of o-Hydroxyphenyl-Substituted Secondary Phosphine Oxides

Wu,

Zhang,

Wang

et al. 2023

J. Org. Chem.

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Palladium‐Catalyzed Asymmetric Trifluoromethylated Allylic Alkylation of N‐Substituted Glycine Ethyl Esters with α‐(Trifluoromethyl)alkenyl Acetates

Zhang

Wang

et al. 2023

Eur J Org Chem

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An efficient strategy for asymmetric trifluoromethylated allylic alkylation of easily available N‐substituted glycine ethyl esters with α‐(trifluoromethyl)alkenyl acetates has been developed. Catalyzed by a [Pd(C3H5)Cl]2/(R)‐BINAP, various trifluoromethyl‐containing N‐substituted glycine ethyl ester derivatives are afforded with good yields and excellent enantioselectivities. The product can be readily converted into diverse fluoro‐substituted species, which shows the practicability of this method.

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Copper‐Catalyzed α,β‐Regioselective (2+4) Cycloaddition of Propargylic Esters

Zhang,

Wu,

Zhong

et al. 2023

Eur J Org Chem

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A copper‐catalyzed α,β‐regioselective (2+4) cycloaddition of propargylic esters with o‐hydroxyphenyl substituted secondary phosphine oxides (SPOs) was established, which afforded a series of phosphorus‐containing six‐membered heterocycles in high yields (up to 99 % yield). This reaction represents the first α,β‐regioselective (2+n) cycloaddition of propargylic esters via the intermediates of copper−allenylidenes, which will enrich the chemistry of propargylic esters and copper−allenylidenes. Moreover, this work also represents the first application of o‐hydroxyphenyl substituted SPOs as 1,4‐dinucleophiles in (2+4) cycloadditions, which provides a useful protocol for the synthesis of phosphorus‐containing six‐membered heterocycles with potential bioactivity.

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Secondary Phosphine Sulfide‐Enabled Iridium‐Catalyzed Asymmetric Allylic Substitution

Cited by 9 publications

References 92 publications

Organocatalytic Diastereoselective (4 + 1) Cycloaddition of o-Hydroxyphenyl-Substituted Secondary Phosphine Oxides

Organocatalytic Diastereoselective (4 + 1) Cycloaddition of o-Hydroxyphenyl-Substituted Secondary Phosphine Oxides

Palladium‐Catalyzed Asymmetric Trifluoromethylated Allylic Alkylation of N‐Substituted Glycine Ethyl Esters with α‐(Trifluoromethyl)alkenyl Acetates

Copper‐Catalyzed α,β‐Regioselective (2+4) Cycloaddition of Propargylic Esters

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