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 inAngewandte Chemie International Edition Vol. 50; no. 33; pp. 7681 - 7685
Main Authors Chen, Guihua, Gui, Jiangyang, Li, Liangchun, Liao, Jian
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 08.08.2011
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
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
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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Summary: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).
Bibliography: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
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SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.201102586