Palladium(II)-Catalyzed\nEnantioselective Ring Opening\nof Oxabenzonorbornadienes via Domino Aminopalladation of Alkynylanilines

We report herein a robust enantioselective ring opening\ncoupling\nof oxabenzonorbornadienes via Pd(II)-catalyzed domino cyclization\nof alkynylanilines, which features the formation of three covalent\nbonds and two contiguous stereocenters with excellent enantio- and\ndiastereoselectivity and a broad substrate scope. The good functional\ngroup tolerance of this domino desymmetrization strategy enables efficient\nlate-stage transformation of natural product-derived alkynylanilines.\nThe resulting indolated dihydronaphthols could serve as a valuable\nplatform to streamline the diversity-oriented synthesis of other valuable\nenantioenriched tetrahydronaphthalene derivatives.

Publication Details

Journal
Figshare
Published
2024-12-30
DOI
https://doi.org/10.1021/acs.orglett.4c04414.s001
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Palladium(II)-Catalyzed\nEnantioselective Ring Opening\nof Oxabenzonorbornadienes via Domino Aminopalladation of Alkynylanilines

Figshare
Catalytic C–H Functionalization Methods
article

Palladium(II)-Catalyzed\nEnantioselective Ring Opening\nof Oxabenzonorbornadienes via Domino Aminopalladation of Alkynylanilines

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Abstract

We report herein a robust enantioselective ring opening\ncoupling\nof oxabenzonorbornadienes via Pd(II)-catalyzed domino cyclization\nof alkynylanilines, which features the formation of three covalent\nbonds and two contiguous stereocenters with excellent enantio- and\ndiastereoselectivity and a broad substrate scope. The good functional\ngroup tolerance of this domino desymmetrization strategy enables efficient\nlate-stage transformation of natural product-derived alkynylanilines.\nThe resulting indolated dihydronaphthols could serve as a valuable\nplatform to streamline the diversity-oriented synthesis of other valuable\nenantioenriched tetrahydronaphthalene derivatives.

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Catalytic C–H Functionalization Methods
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Palladium(II)-Catalyzed\nEnantioselective Ring Opening\nof Oxabenzonorbornadienes via Domino Aminopalladation of Alkynylanilines · Figshare (2024) | TGRS Research Map | TGRS