Stereocontrolled synthesis of bicyclic ureas and sulfamides via Pd-catalyzed alkene carboamination reactions

TETRAHEDRON

卷:75

Article

Babij, Nicholas R.¹  Boothe, Jordan R.¹  McKenna, Grace M.¹  Fornwald, Ryan M.¹  Wolfe, John P.¹ 

[1] Univ Michigan, Dept Chem, 930 N Univ Ave, Ann Arbor, MI 48109 USA

关键词: Palladium;    Alkenes;    Heterocycles;    Stereoselective;   

DOI  :  10.1016/j.tet.2019.04.031

来源: Elsevier

【 摘 要 】

The synthesis of bicyclic ureas and sulfamides via palladium-catalyzed alkene carboamination reactions between aryl/alkenyl halides/triflates and alkenes bearing pendant cyclic sulfamides and ureas is described. The substrates for these reactions are generated in 3-5 steps from commercially available materials, and products are obtained in good yield with up to >20:1 diastereoselectivity. The stereochemical outcome of the sulfamide alkene addition is consistent with a mechanism involving anti-aminopalladation of the alkene, whereas the stereochemical outcome of the urea alkene addition is consistent with a syn-aminopalladation mechanism. (C) 2019 Elsevier Ltd. All rights reserved.

【 授权许可】

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