Construction of Cyclic Sulfamidates Bearing Two gem-Diaryl Stereocenters through a Rhodium-Catalyzed Stepwise Asymmetric Arylation Protocol

A rhodium-catalyzed stepwise asymmetric 1,4- and 1,2-addition of arylboronic acids to α,β-unsaturated cyclic N-sulfonyl ketimines has been developed, providing a wide range of gem-diaryl-substituted chiral benzosulfamidates with high optical purities. C 1-Symmetric chiral diene and branched chiral s...

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Published inOrganic letters Vol. 18; no. 11; pp. 2726 - 2729
Main Authors Zhang, Yu-Fang, Chen, Diao, Chen, Wen-Wen, Xu, Ming-Hua
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.06.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PHOSPHITE-OLEFIN
HIGH-PERFORMANCE
EFFICIENT ACCESS
CHIRAL LIGANDS
SCALE-UP
NUCLEOPHILIC ALLYLATION
ENANTIOSELECTIVE ADDITION
1,4-ADDITION
ARYLBORONIC ACIDS
CONJUGATE ADDITION
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Summary:A rhodium-catalyzed stepwise asymmetric 1,4- and 1,2-addition of arylboronic acids to α,β-unsaturated cyclic N-sulfonyl ketimines has been developed, providing a wide range of gem-diaryl-substituted chiral benzosulfamidates with high optical purities. C 1-Symmetric chiral diene and branched chiral sulfur–olefin ligands were sequentially utilized in this double-arylation process for high stereocontrol. Further synthetic utility offers new opportunities for the facile construction of otherwise difficult to access polycyclic heterocycles.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b01183