Tetrahedron

Ring-closing metathesis strategies to cyclic sulfamide peptidomimetics

JM Dougherty, DA Probst, RE Robinson, JD Moore…

Index: Dougherty, Joseph M; Probst, Donald A; Robinson, Randall E; Moore, Joel D; Klein, Thomas A; Snelgrove, Kelley A; Hanson, Paul R Tetrahedron, 2000 , vol. 56, # 50 p. 9781 - 9790

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Citation Number: 74

Abstract

Ring-closing metathesis (RCM) strategies toward the synthesis of a number of constrained sulfamides are discussed. This approach exploits the inherent chemistry of sulfamides and sulfonyl carbamates to generate both symmetric and unsymmetric cyclic sulfamides. Two strategies are revealed, one centers on the RCM reaction of allylated sulfamides 9a–e to generate the C2-symmetric cyclic sulfamides 4a–e in high yields. A second RCM strategy ...