Rhodium-Catalyzed Highly Enantioselective Addition of Arylboronic Acids to Cyclic Aldimines: Practical Asymmetric Synthesis of Cyclic Sulfamidates

Hui Wang; Ming-Hua Xu

doi:10.1055/s-0033-1338418

Synthesis, Table of Contents

Synthesis 2013; 45(15): 2125-2133
DOI: 10.1055/s-0033-1338418

special topic

Rhodium-Catalyzed Highly Enantioselective Addition of Arylboronic Acids to Cyclic Aldimines: Practical Asymmetric Synthesis of Cyclic Sulfamidates

Hui Wang

Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, P. R. of China Fax: +86(21)50807388 Email: xumh@simm.ac.cn

,

Ming-Hua Xu*

Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, P. R. of China Fax: +86(21)50807388 Email: xumh@simm.ac.cn

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Abstract

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Abstract

A highly efficient asymmetric arylation of cyclic N-sulfonyl aldimines with arylboronic acids catalyzed by a rhodium/ sulfur–olefin ligand complex under mild conditions is described. A wide range 4-aryl-3,4-dihydro-1,2,3-benzoxathiazine 2,2-dioxides were obtained in extremely high yields (93–99%) and high enantiomeric purities (97–99% ee).

Key words

asymmetric catalysis - cyclization - arylation - rhodium - boron - ligands - sulfamidates - heterocycles

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References

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