Synthesis of protected syn 1,3-diols by intramolecular conjugate addition to vinyl sulfones

Laurence Grimaud 1 Delphine Rotulo 1 Rafael Ros-Perez 1 Ludivine Guitry-Azam 1 Joëlle Prunet 1
1 DCSO - Laboratoire de synthèse organique
Abstract : A short route to sulfones 9a-c is described. These synthons encompassing a syn 1,3-diol motif are model compounds for the C16-C24 fragment of Dolabelides. The benzylidene protecting group can be reduced regioselectively to furnish ß-hydroxysulfones 10a-b. First attempts of Julia coupling of the dianions derived from these substrates with aldehydes and ketones are also reported. © 2002 Elsevier Science Ltd. All rights reserved.
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Submitted on : Monday, March 17, 2014 - 9:22:39 PM
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Laurence Grimaud, Delphine Rotulo, Rafael Ros-Perez, Ludivine Guitry-Azam, Joëlle Prunet. Synthesis of protected syn 1,3-diols by intramolecular conjugate addition to vinyl sulfones. Tetrahedron Letters, Elsevier, 2002, 43 (42), pp.7477-7479. ⟨10.1016/s0040-4039(02)01796-3⟩. ⟨hal-00954862⟩

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