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  A Heteroleptic Dirhodium Catalyst for Asymmetric Cyclopropanation with α‐Stannyl α‐Diazoacetate. "Stereoretentive" Stille Coupling with Formation of Chiral Quarternary Carbon Centers

Caló, F. P., & Fürstner, A. (2020). A Heteroleptic Dirhodium Catalyst for Asymmetric Cyclopropanation with α‐Stannyl α‐Diazoacetate. "Stereoretentive" Stille Coupling with Formation of Chiral Quarternary Carbon Centers. Angewandte Chemie International Edition, 59(33), 13900-13907. doi:10.1002/anie.202004377.

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anie202004377-s1-supporting_information_renamed_b260e.pdf (Supplementary material), 11MB
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anie202004377-s1-supporting_information_renamed_b260e.pdf
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 Creators:
Caló, Fabio P.1, Author           
Fürstner, Alois1, Author           
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1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              

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Free keywords: asymmetric catalysis; cyclopropanation; heteroleptic complexes; quarternary chiral centers; rhodium carbenes; Stille coupling
 Abstract: The heteroleptic dirhodium paddlewheel catalyst 7 with a chiral carboxylate/acetamidate ligand sphere is uniquely effective in asymmetric [2+1] cycloadditions with α‐diazo‐α‐trimethylstannyl (silyl, germyl) acetate. Originally discovered as a trace impurity in a sample of the homoleptic parent complex [Rh2((R)‐TPCP)4] (5), it is shown that the protic acetamidate ligand is quintessential for rendering 7 highly enantioselective. The –NH group is thought to lock the ensuing metal carbene in place via interligand hydrogen bonding. The resulting stannylated cyclopropanes undergo “stereoretentive” cross coupling, which shows for the first time that chiral quarternary carbon centers can be made by the Stille‐Migita reaction.

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Language(s): eng - English
 Dates: 2020-05-182020-03-252020-05-192020-05-192020-08-10
 Publication Status: Published in print
 Pages: 8
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.202004377
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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 59 (33) Sequence Number: - Start / End Page: 13900 - 13907 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851