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Enantioselective Sy...
Enantioselective Synthesis of Atropisomeric Biaryls using Biaryl 2,5-Diphenylphospholanes as Ligands for Palladium-Catalysed Suzuki-Miyaura Reactions
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- Byrne, Liam (författare)
- AstraZeneca, Early Chem Dev, R&D, Pharmaceut Sci, Macclesfield, Cheshire, England.
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- Sköld, Christian (författare)
- Uppsala universitet,Läkemedelsdesign och läkemedelsutveckling
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- Norrby, Per-Ola (författare)
- AstraZeneca, R&D, Pharmaceut Sci, Data Sci & Modelling, Gothenburg, Sweden.
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- Munday, Rachel H. (författare)
- AstraZeneca, Chem Dev, Operat, Pharmaceut Technol & Dev, Macclesfield, Cheshire, England.
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- Turner, Andrew R. (författare)
- AstraZeneca, Early Chem Dev, R&D, Pharmaceut Sci, Macclesfield, Cheshire, England.
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- Smith, Peter D. (författare)
- AstraZeneca, Early Chem Dev, R&D, Pharmaceut Sci, Macclesfield, Cheshire, England.
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AstraZeneca, Early Chem Dev, R&D, Pharmaceut Sci, Macclesfield, Cheshire, England Läkemedelsdesign och läkemedelsutveckling (creator_code:org_t)
- 2020-11-22
- 2021
- Engelska.
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Ingår i: Advanced Synthesis and Catalysis. - : John Wiley & Sons. - 1615-4150 .- 1615-4169. ; 363:1, s. 259-267
- Relaterad länk:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Ämnesord
Stäng
- Here we describe the development of biaryl 2,5-diphenylphospholanes as a new class of C-2-symmetric, monodentate ligands for asymmetric Suzuki-Miyaura (ASM) reactions. Screening of a series of exemplary phospholanes led to the identification of two ligands that were used to prepare a range of atropisomeric biaryl and heterobiaryl products with good to excellent levels of enantioselectivity (up to 97:3 e.r.) under mild conditions. DFT studies suggest that the formation of a constraining ligand pocket and coordination of one of the biaryl methoxy groups in the optimised ligands to the metal centre is crucial for restricting conformational freedom in the bond-forming step.
Ämnesord
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Nyckelord
- atropisomeric biaryls
- phospholanes
- palladium
- Suzuki-Miyaura reaction
- Density Functional Theory
Publikations- och innehållstyp
- ref (ämneskategori)
- art (ämneskategori)
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