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ChemInform Abstract: Stereocontrolled Synthesis of Cyclic Ethers by Intramolecular Hetero- Michael Addition. Part 5. Synthesis of All Diastereoisomers of 2,3,5,6- Tetrasubstituted Tetrahydropyrans.

✍ Scribed by J. M. BETANCORT; V. S. MARTIN; J. M. PADRON; J. M. PALAZON; M. A. RAMIREZ; M. A. SOLER

Publisher
John Wiley and Sons
Year
2010
Weight
29 KB
Volume
28
Category
Article
ISSN
0931-7597

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✦ Synopsis

Stereocontrolled Synthesis of Cyclic Ethers by Intramolecular Hetero-Michael Addition. Part 5. Synthesis of All Diastereoisomers of 2,3,5,6-Tetrasubstituted Tetrahydropyrans. -The intramolecular hetero-Michael addition of 7-hydroxy-4-(benzoyloxy)-2,3-unsaturated esters is found to be an excellent way to prepare tetrasubstituted tetrahydropyrans like (I)-(III) of high stereochemical purity. The stereochemical course depends on the reaction conditions. Six of the eight possible diastereomers can be formed directly by hetero-Michael addition and the remaining two are prepared by chemical transformations of the former. -(BETANCORT,

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