A two-step synthesis of allylic syn 1,3-diols via an intramolecular oxa-Michael reaction followed by a modified Julia olefination |
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| Authors: | Raphaë l Oriez |
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| Affiliation: | a Laboratoire de Synthèse Organique, CNRS UMR 7652, Ecole Polytechnique, DCSO, F-91128 Palaiseau, France
b WestCHEM, Department of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow G12 8QQ, UK |
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| Abstract: | 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. |
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