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  Chiral Heterobimetallic Bismuth‐Rhodium Paddlewheel Catalysts: A Conceptually New Approach to Asymmetric Cyclopropanation

Collins, L. R., Auris, S., Goddard, R., & Fürstner, A. (2019). Chiral Heterobimetallic Bismuth‐Rhodium Paddlewheel Catalysts: A Conceptually New Approach to Asymmetric Cyclopropanation. Angewandte Chemie International Edition, 58(11), 3557-3561. doi:10.1002/anie.201900265.

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ange201900265-sup-0001-misc_information.pdf (Supplementary material), 6MB
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ange201900265-sup-0001-misc_information.pdf
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 Creators:
Collins, Lee R.1, Author              
Auris, Sebastian1, Author              
Goddard, Richard2, Author              
Fürstner, Alois1, Author              
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              
2Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              

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Free keywords: bimetallic catalysts; bismuth; carbene complexes; cyclopropanation; rhodium
 Abstract: Cyclopropanation reactions of styrene derivatives with donor/acceptor carbenes formed in situ are significantly more enantioselective when catalyzed by the heterobimetallic bismuth‐rhodium complex 5a endowed with N‐phthalimido tert‐leucine paddlewheel ligands rather than by its homobimetallic dirhodium analogue 1a. This virtue is likely the result of two synergizing factors: the conical shape of 5a translates into a narrower calyx‐like chiral binding site about the catalytically active Rh center; the Bi atom, although fully solvent exposed, does not decompose aryl diazoacetates and is hence incapable of promoting a racemic background reaction. Moreover, ligand variation proved that successful catalyst design mandates that the anisotropy of the conical heterobimetallic core be matched by proper directionality within the ligand sphere.

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Language(s): eng - English
 Dates: 2019-01-082019-01-232019-02-142019-03-11
 Publication Status: Published in print
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201900265
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Title: Angewandte Chemie International Edition
  Other : Angewandte Chemie, International Edition
  Other : Angew. Chem. Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 58 (11) Sequence Number: - Start / End Page: 3557 - 3561 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851