N‐Heterocyclic Carbene (NHC) Catalyzed Cycloaddition of CO<sub>2</sub> to <i>N</i>‐Tosyl Aziridines: Regio and Stereoselective Synthesis of Oxazolidin‐2‐ones

Seayad, Jayasree; Seayad, Abdul Majeed; Ng, Joseph Kok Peng; Chai, Christina L. L.

doi:10.1002/cctc.201200080

Cited by 56 publications

(18 citation statements)

References 46 publications

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“…N-Heterocyclic carbene (NHC) 283-catalyzed highly regio-and stereoselective carboxylation of N-tosylaziridines 10 with CO 2 leads to the formation of 3,5-disubstituted and 3,4,5-trisubstituted oxazolidin-2-ones (284 and 285) in good yields [129]. It has also been observed that the insertion of CO 2 in 2-alkyl-Ntosylaziridine is possible to produce oxazolidinone compound without any catalyst, solvent, high temperature, or pressure, when high-speed ball milling has been applied (Scheme 72) [130].…”

Section: Synthesis Of Oxazolidines Oxazolines and Oxazolesmentioning

confidence: 99%

Ring Expansions of Activated Aziridines and Azetidines

Ghorai

Bhattacharyya

Das

et al. 2015

Topics in Heterocyclic Chemistry

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Facile construction of small and normal-sized, or more precisely, four to seven-membered aza-heterocyclic ring systems is always a challenging yet rewarding task for the synthetic organic chemists. Fortunately, activated aziridines and azetidines provide a direct and convenient access to this coveted molecular architectures through several elegant ring-expansion approaches. This chapter presents some of the illustrative and contemporary examples to demonstrate the synthetic diversity and efficiency of the ring-expansion strategies of activated aziridines and azetidines towards a vast array of small to normal-sized aza-heterocyclic moieties.

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Section: Synthesis Of Oxazolidines Oxazolines and Oxazolesmentioning

confidence: 99%

Ring Expansions of Activated Aziridines and Azetidines

Ghorai

Bhattacharyya

Das

et al. 2015

Topics in Heterocyclic Chemistry

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“…(45-1)]. [261] The application of this methodology for the stereoselective synthesis of (4R,5R)-4-methyl-5-phenyloxazolidin-2-one, a well-known chiral auxiliary, was also demonstrated [Eq. ].…”

Section: Cycloaddition Of Epoxides Catalyzed By Nhc-co 2 Adductsmentioning

confidence: 99%

Recent Advances in Carbon Dioxide Capture, Fixation, and Activation by using N‐Heterocyclic Carbenes

2014

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In the last two decades, CO2 emission has caused a lot of environmental problems. To mitigate the concentration of CO2 in the atmosphere, various strategies have been implemented, one of which is the use of N-heterocyclic carbenes (NHCs) and related complexes to accomplish the capture, fixation, and activation of CO2 effectively. In this review, we summarize CO2 capture, fixation, and activation by utilizing NHCs and related complexes; homogeneous reactions and their reaction mechanisms are discussed. Free NHCs and NHC salts can capture CO2 in both direct and indirect ways to form imidazolium carboxylates, and they can also catalyze the reaction of aromatic aldehydes with CO2 to form carboxylic acids and derivatives. Moreover, associated with transition metals (TMs), NHCs can form NHC-TM complexes to transform CO2 into industrial acid or esters. Non-metal-NHC complexes can also catalyze the reactions of silicon and boron complexes with CO2 . In addition, catalytic cycloaddition of epoxides with CO2 is another effective function of NHC complexes, and NHC ionic liquids perform excellently in this aspect.

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“…Chirality transfer from enantiopure aziridines provides enantioenriched products. 35,54 This transformation can give two different isomers (Scheme 18), but ionic liquids, 81 NHCs, 82 Cr-salen, 83 and Alsalen/ammonium salt, 35 favour the 5-substituted isomer (if the nitrogen is substituted and R ' = Ph).…”

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confidence: 99%

Enantioselective Incorporation of CO₂: Status and Potential

et al. 2017

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CO2 is a promising and sustainable carbon feedstock for organic synthesis. New catalytic protocols for efficient incorporation of CO2 into organic molecules are continuously reported. However, little progress has been made in the enantioselective conversion of CO2 to form enantioenriched molecules. In order to allow CO2 to become a versatile carbon source in academia, and in the fine chemical and pharmaceutical industries, the development of enantioselective approaches is essential. Here we discuss general strategies for CO2 activation and for generation of enantioenriched molecules, alongside selected examples of reactions involving asymmetric incorporation of CO2. Main product classes considered are carboxylic acids and derivatives (C-2 CO2 bonds), and carbonates, carbamates, and polycarbonates (C-OCO bonds). Similarities to asymmetric hydrogenation are discussed, and some strategies for developing novel enantioselective CO2 reactions are outlined.

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N‐Heterocyclic Carbene (NHC) Catalyzed Cycloaddition of CO₂ to N‐Tosyl Aziridines: Regio and Stereoselective Synthesis of Oxazolidin‐2‐ones

Cited by 56 publications

References 46 publications

Ring Expansions of Activated Aziridines and Azetidines

Ring Expansions of Activated Aziridines and Azetidines

Recent Advances in Carbon Dioxide Capture, Fixation, and Activation by using N‐Heterocyclic Carbenes

Enantioselective Incorporation of CO₂: Status and Potential

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N‐Heterocyclic Carbene (NHC) Catalyzed Cycloaddition of CO2 to N‐Tosyl Aziridines: Regio and Stereoselective Synthesis of Oxazolidin‐2‐ones

Cited by 56 publications

References 46 publications

Ring Expansions of Activated Aziridines and Azetidines

Ring Expansions of Activated Aziridines and Azetidines

Recent Advances in Carbon Dioxide Capture, Fixation, and Activation by using N‐Heterocyclic Carbenes

Enantioselective Incorporation of CO2: Status and Potential

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N‐Heterocyclic Carbene (NHC) Catalyzed Cycloaddition of CO₂ to N‐Tosyl Aziridines: Regio and Stereoselective Synthesis of Oxazolidin‐2‐ones

Enantioselective Incorporation of CO₂: Status and Potential