Chiral Thiourea Catalyzed Asymmetric Henry Reaction: Construction of Stereogenic Center Bearing a CF<sub>3</sub> Group from 2,2,2-Trifluoroacetophenone Substrates

吴丽丽,; 苏瀛鹏,; 种思颖,; 张为钢,; 黄丹凤,; 王克虎,; 胡雨来,

doi:10.6023/cjoc201612006

Cited by 3 publications

(1 citation statement)

References 3 publications

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“…[22] While copper continues to be the preferred metal due to its inexpensive and less toxic nature together with prominent result in most cases. [23～29] Concerning the chiral ligands, since the pioneering work of Jørgensen [23,30] and Evans, [31] bisoxazolines, [32～37] bisoxa-zolidines, [38,39] boron-bridged bisoxazolines, [40] chiral diamines, [41～45] sulfonyldiamine, [26,46] thioure [47,48] and pyridine derivatives, [49～51] etc. have been tested in the asymmetric Henry reaction.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Chiral Imidazole Amino Alcohols and Their Application in the Asymmetric Copper-Catalyzed Henry Reaction

Mao¹,

Yang²,

Xiao³

et al. 2019

Chin. J. Org. Chem.

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Using L-phenylalaninol as chiral precursor, a series of multi-aryl substituted imidazole amino alcohol derivatives containing appended chiral functionalities were synthesized through a "four component-one pot procedure" from the condensation reaction of L-phenylalaninol, dibenzoyl (benzil), ammonium acetate and different heterocyclic aryl-aldehyde. X-ray crystal analysis confirmed that the chiral carbon retained the S configuration of L-phenylalaninol. The chiral ligands in combination with Cu(OAc) 2 •H 2 O catalyzed the enantioselective Henry reaction of nitromethane and aromatic aldehydes with moderate to high yields and excellent enantioselectivities (＞99%) with S configuration. The easy availability of catalyst components, mild reaction conditions and high enantioselectivity make the system attractive for practical application.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Chiral Imidazole Amino Alcohols and Their Application in the Asymmetric Copper-Catalyzed Henry Reaction

Mao¹,

Yang²,

Xiao³

et al. 2019

Chin. J. Org. Chem.

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Copper(I)‐Catalyzed Asymmetric [3+2]‐Cycloaddition of α‐Substituted Iminoesters with α‐Trifluoromethyl α,β‐Unsaturated Esters

Liu

Zhang

et al. 2018

Chin. J. Chem.

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Reported herein is an example of highly regio-, diastereo-and enantioselective Cu(I)-catalyzed intermolecular [3+2] cycloaddition reaction of α-substituted iminoesters with α-trifluoromethyl α,-unsaturated esters. This novel strategy provided a facile access to pyrrolidines with two skipped (aza)quaternary stereocenters including a CF 3 all-carbon quaternary stereocenter. A broad substrate scope was observed and high yields (up to 94%) with excellent diastereoselectivity (up to ＞20 : 1 d.r.) and enantioselectivity (up to 98% ee) were obtained.

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An Unexpected Inactivation of N-Heterocyclic Carbene Organic Catalyst by 1-Methylcyclopropylcarbaldehyde and 2,2,2-Trifluoroacetophenone

Chen

Pan

et al. 2022

Front. Chem.

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An unprecedented inactivation process of the indanol-derived NHC catalysts bearing N-C6F5 groups is reported. An unexpected multi-cyclic complex product is obtained from the 3-component reaction with the 1-methylcyclopropyl-carbaldehyde, the 2,2,2-trifluoroacetophenone and the NHC catalyst. The absolute structure of the inactivation product is unambiguously assigned via X-ray analysis on its single crystals. The formation of the structurally complex product is rationalized through a multi-step cascade cyclization process.

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Chiral Thiourea Catalyzed Asymmetric Henry Reaction: Construction of Stereogenic Center Bearing a CF₃ Group from 2,2,2-Trifluoroacetophenone Substrates

Abstract: An asymmetric Henry reaction with 2,2,2-trifluoroacetophenone as trifluoromethyl building block was described. This reaction was catalyzed by bifunctional thiourea derived from quinine to give the product bearing a CF 3 stereogenic center in good yield with good enantioselectivity.

Cited by 3 publications

References 3 publications

Synthesis of Chiral Imidazole Amino Alcohols and Their Application in the Asymmetric Copper-Catalyzed Henry Reaction

Synthesis of Chiral Imidazole Amino Alcohols and Their Application in the Asymmetric Copper-Catalyzed Henry Reaction

Copper(I)‐Catalyzed Asymmetric [3+2]‐Cycloaddition of α‐Substituted Iminoesters with α‐Trifluoromethyl α,β‐Unsaturated Esters

An Unexpected Inactivation of N-Heterocyclic Carbene Organic Catalyst by 1-Methylcyclopropylcarbaldehyde and 2,2,2-Trifluoroacetophenone

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Chiral Thiourea Catalyzed Asymmetric Henry Reaction: Construction of Stereogenic Center Bearing a CF3 Group from 2,2,2-Trifluoroacetophenone Substrates

Abstract: An asymmetric Henry reaction with 2,2,2-trifluoroacetophenone as trifluoromethyl building block was described. This reaction was catalyzed by bifunctional thiourea derived from quinine to give the product bearing a CF 3 stereogenic center in good yield with good enantioselectivity.

Cited by 3 publications

References 3 publications

Synthesis of Chiral Imidazole Amino Alcohols and Their Application in the Asymmetric Copper-Catalyzed Henry Reaction

Synthesis of Chiral Imidazole Amino Alcohols and Their Application in the Asymmetric Copper-Catalyzed Henry Reaction

Copper(I)‐Catalyzed Asymmetric [3+2]‐Cycloaddition of α‐Substituted Iminoesters with α‐Trifluoromethyl α,β‐Unsaturated Esters

An Unexpected Inactivation of N-Heterocyclic Carbene Organic Catalyst by 1-Methylcyclopropylcarbaldehyde and 2,2,2-Trifluoroacetophenone

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Chiral Thiourea Catalyzed Asymmetric Henry Reaction: Construction of Stereogenic Center Bearing a CF₃ Group from 2,2,2-Trifluoroacetophenone Substrates