O2‐Assisted Four‐Component Reaction of Vinyl Magnesium Bromide with Chiral N‐tert‐Butanesulfinyl Imines To Form syn‐1,3‐Amino Alcohols

Wang, Runping; Luo, Jingfan; Zheng, Chunmei; Zhang, Hongyun; L, Gao; Song, Zhenlei

doi:10.1002/anie.202109566

Angew Chem Int Ed

2021

DOI: 10.1002/anie.202109566

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O₂‐Assisted Four‐Component Reaction of Vinyl Magnesium Bromide with Chiral N‐tert‐Butanesulfinyl Imines To Form syn‐1,3‐Amino Alcohols

Runping Wang

Jingfan Luo

Chunmei Zheng

et al.

Abstract: An O 2 -assisted, four-component reaction has been developed to synthesizeawide range of syn-1,3-amino alcohols in one step.T he reaction proceeds by oxygenation of vinyl magnesium bromide (component-I) with O 2 (component-II) to give am agnesium enolate of acetaldehyde,w hich undergoes addition to ac hiral N-tert-butanesulfinyl imine (component-III) followed by asequential addition with excess vinyl magnesium bromide (component-IV). The approach allows diastereoselective synthesis of anti/syn-and syn/syn-3ami… Show more

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Cited by 4 publications

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Regio‐ and Diastereoselective Conjugate Addition of Grignard Reagents to Chiral Fluoroalkyl α,β‐Unsaturated N‐tert‐Butanesulfinyl Ketimines: Synthesis of Optically Active Fluorinated Enamines and Derivatives

Ma,

Liu,

Liao

et al. 2023

Adv Synth Catal

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A regio‐ and diastereoselective conjugate addition reaction of Grignard reagents to fluoroalkyl α,β‐unsaturated N‐tert‐butanesulfinyl ketimines was disclosed. A range of different fluoroalkyls and Grignard reagents were well tolerated, giving up to 99% diastereomeric and regioisomeric ratios. This reaction provided a straightforward method for the synthesis of a variety of enantiomerically enriched α‐fluorinated enamines and derivatives which are difficult to achieve with other methods.

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Regio‐ and Diastereoselective Conjugate Addition of Grignard Reagents to Chiral Fluoroalkyl α,β‐Unsaturated N‐tert‐Butanesulfinyl Ketimines: Synthesis of Optically Active Fluorinated Enamines and Derivatives

Ma,

Liu,

Liao

et al. 2023

Adv Synth Catal

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Divergent Auto‐oxidative Alkylation and Alkanoacylation of Quinoxalin‐2(1H)‐ones with Aliphatic Aldehydes

Shen

et al. 2022

Asian J Org Chem

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Auto-oxidation of aliphatic aldehydes generates alkyl radicals and alkanoyl radicals, which can be intercepted to generate carbon-carbon bonds. However, the highly reactive and unstable radical intermediates make the controlling selectivity alkylation and alkanoacylation especially challenging. Herein, we report a sustainable and controllable protocol for the auto-oxidative alkylation and alkanoacylation of quinoxalin-2(1H)-ones with good reactivity and selectivity. This protocol was presented in a green and sustainable manner, using oxygen as the only oxidant, avoiding the use of catalysts and explosive oxidants. It offers a new paradigm for a convenient, green synthesis of alkyl and alkanoyl compounds from abundant aliphatic aldehydes.

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Divergent Synthesis, Antiproliferative and Antimicrobial Studies of 1,3‐Aminoalcohol and 3‐Amino‐1,2‐Diol Based Diaminopyrimidines

Raji

Huỳnh

et al. 2022

Chemistry & Biodiversity

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A series of novel diaminopyrimidines containing pinane moieties were synthesized via an efficient methodology starting from pinane‐based aminoalcohols, aminodiols and 2,4‐dichloropyrimidines. Bioassay tests demonstrated that compound 18a displayed much stronger antiproliferative activities against four human cancer cell lines (HeLa, Siha, MDA‐MB‐231, MCF‐7 and A2780) than positive control cisplatin. In particular, compound 22a was found to be selective in inhibiting HeLa cell proliferation with cancer cell growth inhibition values higher than 95 %. Moreover, the in vitro screening of prepared compounds against different bacterial and fungal strains is reported. The results revealed that 12b and 17a, the most promising compounds, displayed selective inhibition for the Gram‐positive bacteria (B. subtilis and S. aureus) with percent inhibition values ranging from 75 to 95 % at 10 μg/mL concentration. Both selective inhibition and the in vitro activity values demonstrated that these compounds have the potential to be developed into clinically important therapeutic choices for the treatment of infections caused by B. subtilis and S. aureus.

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O₂‐Assisted Four‐Component Reaction of Vinyl Magnesium Bromide with Chiral N‐tert‐Butanesulfinyl Imines To Form syn‐1,3‐Amino Alcohols

Cited by 4 publications

References 74 publications

Regio‐ and Diastereoselective Conjugate Addition of Grignard Reagents to Chiral Fluoroalkyl α,β‐Unsaturated N‐tert‐Butanesulfinyl Ketimines: Synthesis of Optically Active Fluorinated Enamines and Derivatives

Regio‐ and Diastereoselective Conjugate Addition of Grignard Reagents to Chiral Fluoroalkyl α,β‐Unsaturated N‐tert‐Butanesulfinyl Ketimines: Synthesis of Optically Active Fluorinated Enamines and Derivatives

Divergent Auto‐oxidative Alkylation and Alkanoacylation of Quinoxalin‐2(1H)‐ones with Aliphatic Aldehydes

Divergent Synthesis, Antiproliferative and Antimicrobial Studies of 1,3‐Aminoalcohol and 3‐Amino‐1,2‐Diol Based Diaminopyrimidines

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