Chiral Sulfoxide-Olefin Ligands: Completely Switchable Stereoselectivity in Rhodium-Catalyzed Asymmetric Conjugate Additions
Have it both ways: A novel class of chiral sulfoxide‐olefin ligands was synthesized from a single chiral source. These ligands were evaluated in rhodium‐catalyzed 1,4‐additions of arylboronic acids to electron‐deficient olefins, and remarkable olefin‐directed reversal of stereoselectivity (up to >...
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Published in | Angewandte Chemie International Edition Vol. 50; no. 33; pp. 7681 - 7685 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
Weinheim
WILEY-VCH Verlag
08.08.2011
WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc |
Edition | International ed. in English |
Subjects | |
Online Access | Get full text |
ISSN | 1433-7851 1521-3773 1521-3773 |
DOI | 10.1002/anie.201102586 |
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Abstract | Have it both ways: A novel class of chiral sulfoxide‐olefin ligands was synthesized from a single chiral source. These ligands were evaluated in rhodium‐catalyzed 1,4‐additions of arylboronic acids to electron‐deficient olefins, and remarkable olefin‐directed reversal of stereoselectivity (up to >99 % ee, R isomer; 98 % ee, S isomer) was observed when the reversal ligand pair L1 (branched olefin) and L2 (linear olefin) were utilized (see scheme). |
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AbstractList | Have it both ways: A novel class of chiral sulfoxide‐olefin ligands was synthesized from a single chiral source. These ligands were evaluated in rhodium‐catalyzed 1,4‐additions of arylboronic acids to electron‐deficient olefins, and remarkable olefin‐directed reversal of stereoselectivity (up to >99 % ee, R isomer; 98 % ee, S isomer) was observed when the reversal ligand pair L1 (branched olefin) and L2 (linear olefin) were utilized (see scheme). |
Author | Gui, Jiangyang Liao, Jian Li, Liangchun Chen, Guihua |
Author_xml | – sequence: 1 givenname: Guihua surname: Chen fullname: Chen, Guihua organization: Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (China) – sequence: 2 givenname: Jiangyang surname: Gui fullname: Gui, Jiangyang organization: Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (China) – sequence: 3 givenname: Liangchun surname: Li fullname: Li, Liangchun organization: Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (China) – sequence: 4 givenname: Jian surname: Liao fullname: Liao, Jian email: jliao@cib.ac.cn organization: Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (China) |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/21726029$$D View this record in MEDLINE/PubMed |
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Keywords | chirality STEERING LIGANDS ENANTIOSELECTIVITY S ligands COMPLEXES conjugate addition ARYLBORONIC ACIDS REVERSAL BORONIC ACIDS TERT-BUTANESULFINYL IMINES ENANTIOFACIAL SELECTIVITY stereoselectivity reversal DIENE LIGANDS 1,4-ADDITION rhodium |
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Notes | ArticleID:ANIE201102586 CAS Jiangxi Key Laboratory of Functional Organic Molecules ark:/67375/WNG-FBTXHCRP-G Chengdu Institute of Biology of CAS - No. Y0B1051100 Major State Basic Research Development Program - No. 2010CB833300 istex:8E973D5D92E901546824D8993E7A098967356C58 We thank the NSFC(No. 21072186 and 20872139), CAS, Chengdu Institute of Biology of CAS (Y0B1051100), the Major State Basic Research Development Program (973 program, 2010CB833300), and Jiangxi Key Laboratory of Functional Organic Molecules. NSFC - No. 21072186; No. 20872139 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23 |
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Snippet | Have it both ways: A novel class of chiral sulfoxide‐olefin ligands was synthesized from a single chiral source. These ligands were evaluated in... |
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SubjectTerms | Alkenes - chemistry Catalysis Chemistry Chemistry, Multidisciplinary chirality conjugate addition Crystallography, X-Ray Ligands Models, Molecular Molecular Structure Organometallic Compounds - chemistry Physical Sciences Rhodium Rhodium - chemistry S ligands Safrole - analogs & derivatives Safrole - chemical synthesis Safrole - chemistry Science & Technology Stereoisomerism stereoselectivity reversal |
Title | Chiral Sulfoxide-Olefin Ligands: Completely Switchable Stereoselectivity in Rhodium-Catalyzed Asymmetric Conjugate Additions |
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