A C(2)-symmetric chiral bis-sulfoxide ligand in a rhodium-catalyzed reaction: asymmetric 1,4-addition of sodium tetraarylborates to chromenones

A new C(2)-symmetric chiral bis-sulfoxide ligand, (R,R)-1,2-bis(tert-butylsulfinyl)benzene, has been designed and prepared by the reaction of (R)-benzyl tert-butylsulfoxide with (R)-thiosulfinate. This ligand exhibits excellent enantioselectivities in the Rh-catalyzed asymmetric 1,4-addition reactio...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2010-04, Vol.132 (13), p.4552-4553
Main Authors: Chen, Jun, Chen, Junmin, Lang, Feng, Zhang, Xiangyang, Cun, Linfeng, Zhu, Jin, Deng, Jingen, Liao, Jian
Format: Article
Language:English
Subjects:
Borates - chemistry
Catalysis
Chromones - chemical synthesis
Chromones - chemistry
Ligands
Molecular Structure
Organometallic Compounds - chemistry
Rhodium - chemistry
Stereoisomerism
Sulfoxides - chemical synthesis
Sulfoxides - chemistry
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Summary:A new C(2)-symmetric chiral bis-sulfoxide ligand, (R,R)-1,2-bis(tert-butylsulfinyl)benzene, has been designed and prepared by the reaction of (R)-benzyl tert-butylsulfoxide with (R)-thiosulfinate. This ligand exhibits excellent enantioselectivities in the Rh-catalyzed asymmetric 1,4-addition reaction. In particular, the present work has realized access to optically pure flavanones for the first time through 1,4-addition of arylboronic reagents to chromenones.
ISSN:1520-5126
DOI:10.1021/ja1005477