Synthesis of chiral (7R)-[η6-5-(N,N-dimethylamino)-7-formyl-1,3-benzodioxole]chromium complex and its application in the synthesis of optically active cis-β-lactams

Anew strategy for the coupling of abroad scope of electronically diverse aromatics to boronic esters is reported. The coupling sequence,w hich relies on the directed ortholithiation of chromium arene complexes followed by boronate formation and oxidation, occurs with complete ortho-selectivity and enantiospecificity to give the coupling products in excellent yields and with high functional group tolerance.A n intermediate chromiuma rene boronate complex was characterizedb yX -ray,N MR, and IR experiments to elucidate the reaction mechanism.

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ortho‐Directing Chromium Arene Complexes as Efficient Mediators for Enantiospecific C(sp²)–C(sp³) Cross‐Coupling Reactions

Bigler

Aggarwal

2018

Angew Chem Int Ed

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A new strategy for the coupling of a broad scope of electronically diverse aromatics to boronic esters is reported. The coupling sequence, which relies on the directed ortho-lithiation of chromium arene complexes followed by boronate formation and oxidation, occurs with complete ortho-selectivity and enantiospecificity to give the coupling products in excellent yields and with high functional group tolerance. An intermediate chromium arene boronate complex was characterized by X-ray, NMR, and IR experiments to elucidate the reaction mechanism.

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Synthesis of chiral (7R)-[η6-5-(N,N-dimethylamino)-7-formyl-1,3-benzodioxole]chromium complex and its application in the synthesis of optically active cis-β-lactams

Cited by 14 publications

References 76 publications

Chromium‐Arene Complexes

Chromium‐Arene Complexes

ortho‐Directing Chromium Arene Complexes as Efficient Mediators for Enantiospecific C(sp²)–C(sp³) Cross‐Coupling Reactions

ortho‐Directing Chromium Arene Complexes as Efficient Mediators for Enantiospecific C(sp²)–C(sp³) Cross‐Coupling Reactions

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Synthesis of chiral (7R)-[η6-5-(N,N-dimethylamino)-7-formyl-1,3-benzodioxole]chromium complex and its application in the synthesis of optically active cis-β-lactams

Cited by 14 publications

References 76 publications

Chromium‐Arene Complexes

Chromium‐Arene Complexes

ortho‐Directing Chromium Arene Complexes as Efficient Mediators for Enantiospecific C(sp2)–C(sp3) Cross‐Coupling Reactions

ortho‐Directing Chromium Arene Complexes as Efficient Mediators for Enantiospecific C(sp2)–C(sp3) Cross‐Coupling Reactions

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Product

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About

ortho‐Directing Chromium Arene Complexes as Efficient Mediators for Enantiospecific C(sp²)–C(sp³) Cross‐Coupling Reactions

ortho‐Directing Chromium Arene Complexes as Efficient Mediators for Enantiospecific C(sp²)–C(sp³) Cross‐Coupling Reactions