A two-step synthesis of allylic syn 1,3-diols via an intramolecular oxa-Michael reaction followed by a modified Julia olefination

Raphaël Oriez (1) , Joëlle Prunet (2)

1 DCSO - Laboratoire de synthèse organique
2 Department of Chemistry

A two-step process for the synthesis of allylic syn 1,3-diols is developed. An intramolecular oxa-Michael reaction onto vinyl heteroaromatic sulfones allows the diastereoselective formation of 1-sulfonyl 2,4-diols protected as benzylidene acetals. These sulfones are then engaged in a modified Julia olefination to furnish the olefins contiguous to the benzylidene acetal ring with good E/Z selectivity. © 2009.

Raphaël Oriez, Joëlle Prunet. A two-step synthesis of allylic syn 1,3-diols via an intramolecular oxa-Michael reaction followed by a modified Julia olefination. Tetrahedron Letters, 2010, 51 (2), pp.256-258. ⟨10.1016/j.tetlet.2009.10.139⟩. ⟨hal-00951249⟩