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Catalytic Asymmetric Synthesis of Cyclic Sulfamides from Conjugated Dienes

Richard G. Cornwall, Baoguo Zhao and Yian Shi*

*Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, Email: yianlamar.colostate.edu

R. G. Cornwall, B. Zhao, Y. Shi, Org. Lett., 2013, 15, 796-799.

DOI: 10.1021/ol303469a


Abstract

A catalytic asymmetric diamination of alkyl dienes using N,N′-di-tert-butylthiadiaziridine 1,1-dioxide in the presence of Pd(0) and a chiral phosphoramidite ligand gives cyclic sulfamides in high yield and high ee. The diamination is also amenable to gram scale.

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Diamination of Conjugated Dienes and Trienes Catalyzed by N-Heterocyclic Carbene-Pd(0) Complexes

L. Xu, H. Du, Y. Shi, J. Org. Chem., 2007, 72, 7038-7041.


Key Words

1,2-diamination


ID: J54-Y2013-0420