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Solid-phase synthesis of functionalized tropane derivatives via 1,3-dipolar cycloaddition

Sandrine Caix-Haumesser 1 Issam Hanna 1 Jean-Yves Lallemand 1 Jean-François Peyronel 2
1 DCSO - Laboratoire de synthèse organique
2 Aventis Pharma
Abstract : 1,3-Dipolar cycloaddition of 3-oxidopyridinium betaine to activated olefins on solid-phase leads to resin-bound 8-azabicyclo[3.2.1]octenones which undergo further transformations such as 1,4-addition of nucleophiles. Cleavage of benzyl linker is achieved using acid chlorides in the presence of potassium iodide to give substituted tropane derivatives. © 2001 Elsevier Science Ltd.
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Submitted on : Wednesday, March 12, 2014 - 9:41:54 PM
Last modification on : Thursday, March 5, 2020 - 6:25:48 PM

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Sandrine Caix-Haumesser, Issam Hanna, Jean-Yves Lallemand, Jean-François Peyronel. Solid-phase synthesis of functionalized tropane derivatives via 1,3-dipolar cycloaddition. Tetrahedron Letters, Elsevier, 2001, 42 (22), pp.3721-3723. ⟨10.1016/s0040-4039(01)00565-2⟩. ⟨hal-00954879⟩

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