Practical access to axially chiral sulfonamides and biaryl amino phenols via organocatalytic atroposelective N-alkylation

Shenci Lu, Shawn Voon Hwee Ng, Kaitlyn Lovato, Jun-Yang Ong, Si Bei Poh, Xiao Qian Ng, László Kürti () and Yu Zhao ()
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Shenci Lu: Northwestern Polytechnical University
Shawn Voon Hwee Ng: National University of Singapore
Kaitlyn Lovato: Rice University BioScience Research Collaborative
Jun-Yang Ong: National University of Singapore
Si Bei Poh: National University of Singapore
Xiao Qian Ng: National University of Singapore
László Kürti: Rice University BioScience Research Collaborative
Yu Zhao: National University of Singapore

Nature Communications, 2019, vol. 10, issue 1, 1-10

Abstract: Abstract The importance of axial chirality in enantioselective synthesis has been widely recognized for decades. The practical access to certain structures such as biaryl amino phenols known as NOBINs in enantiopure form, however, still remains a challenge. In drug delivery, the incorporation of axially chiral molecules in systematic screening has also received a great deal of interest in recent years, which calls for innovation and practical synthesis of structurally different axially chiral entities. Herein we present an operationally simple catalytic N-alkylation of sulfonamides using commercially available chiral amine catalysts to deliver two important classes of axially chiral compounds: structurally diverse NOBIN analogs as well as axially chiral N-aryl sulfonamides in excellent enantiopurity. Structurally related chiral sulfonamide has shown great potential in drug molecules but enantioselective synthesis of them has never been accomplished before. The practical catalytic procedures of our methods also bode well for their wide application in enantioselective synthesis.

Date: 2019
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DOI: 10.1038/s41467-019-10940-4

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