0000000001315540

AUTHOR

He Sheng

showing 5 related works from this author

Control of N-Heterocyclic Carbene Catalyzed Reactions of Enals: Asymmetric Synthesis of Oxindole-γ-Amino Acid Derivatives.

2017

A strategy to control the switch between a non‐cycloaddition reaction and a cycloaddition reaction of enals, using N‐heterocyclic carbene (NHC) catalyisis, has been developed. The new scalable protocol leads to γ‐amino‐acid esters bearing a tetrasubstituted stereocenter in good yields and high stereoselectivities by homo‐Mannich reactions of enals and isatin‐derived ketimines. By simply changing the N‐ketimine substituent to an ortho‐hydroxy phenyl group, the corresponding spirocyclic oxindolo‐γ‐lactams are obtained. peerReviewed

StereochemistrySubstituent010402 general chemistry01 natural sciencesCatalysisStereocenterCatalysischemistry.chemical_compoundaldehyditaldehydesPhenyl groupOxindoleta116orgaaniset yhdisteetkemiallinen synteesi010405 organic chemistryEnantioselective synthesisGeneral MedicineGeneral ChemistryCycloaddition0104 chemical scienceschemistryorganic compoundsCarbenechemical synthesisAngewandte Chemie (International ed. in English)
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N-Heterocyclic Carbene Catalyzed [3+2] Cycloaddition of Enals with Masked Cinnamates for the Asymmetric One-Pot Synthesis of Adipic Acid Derivatives.

2017

A novel short entry to 3,4-disubstituted adipic acids has been developed by employing an asymmetric NHC-catalyzed [3+2] cycloaddition of enals with masked cinnammates in moderate to good yields and high stereoselectivities. The synthetic utility of the protocol was demonstrated by the basic conversion of the masked cyclopentanone intermediates to 3S,4S-disubstituted adipic acid precursors of pharmaceutically important gababutins.

AdipatesOne-pot synthesishapotCyclopentanes010402 general chemistryCyclopentanone01 natural sciencesCatalysisCatalysischemistry.chemical_compoundOrganic chemistryCinnamatesorganocatalysista116cycloadditionadipic acidAdipic acidCycloaddition ReactionMolecular Structure010405 organic chemistryOrganic ChemistrygababutinsStereoisomerismGeneral ChemistryCycloaddition0104 chemical scienceschemistryCinnamatesOrganocatalysisorgaaninen kemiaCarbeneN-heterocyclic carbeneMethaneChemistry (Weinheim an der Bergstrasse, Germany)
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N-Heterocyclic Carbene Catalyzed Asymmetric Synthesis of Dihydropyranothiazoles­ via Azolium Enolate Intermediates

2017

A highly diastereo- and enantiostereoselective synthesis of bicyclic dihydropyranothiazoles combining a thiazole and δ-lactone skeleton via NHC-catalyzed [4+2] annulation of 5-alkenylthiazolones and α-chloroaldehydes has been developed. The heterocyclic products are formed via azolium enolate intermediates in good yields with high diastereo- and enantistereoselectivities.

AnnulationBicyclic molecule010405 organic chemistryStereochemistryOrganic ChemistryEnantioselective synthesis010402 general chemistry01 natural sciencesCatalysis0104 chemical sciencesCatalysischemistry.chemical_compoundchemistryOrganocatalysisThiazoleCarbeneSynthesis
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CCDC 1561240: Experimental Crystal Structure Determination

2017

Related Article: Xiang-Yu Chen, Sun Li, He Sheng, Qiang Liu, Ehsan Jafari, Carolina von Essen, Kari Rissanen, Dieter Enders|2017|Chem.-Eur.J.|23|13042|doi:10.1002/chem.201703579

Space GroupCrystallography3-(4-fluorophenyl)-2-(3-methyl-4-nitro-12-oxazol-5-yl)-4-phenylcyclopentan-1-oneCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1571777: Experimental Crystal Structure Determination

2017

Related Article: Xiang-Yu Chen, Jia-Wen Xiong, Qiang Liu, Sun Li, He Sheng, Carolina von Essen, Kari Rissanen, Dieter Enders|2018|Angew.Chem.,Int.Ed.|57|300|doi:10.1002/anie.201708994

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parametersmethyl 3-{1-benzyl-5-bromo-3-[(3-bromophenyl)amino]-2-oxo-23-dihydro-1H-indol-3-yl}-3-phenylpropanoate propan-2-ol solvateExperimental 3D Coordinates
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