Synthesis 2013; 45(15): 2125-2133
DOI: 10.1055/s-0033-1338418
special topic
© Georg Thieme Verlag Stuttgart · New York

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
› Author Affiliations
Further Information

Publication History

Received: 21 February 2013

Accepted after revision: 25 March 2013

Publication Date:
08 May 2013 (eFirst)

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).

Supporting Information

 
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