Stereoselective synthesis of cis-fused chlorinated bicyclic ethers via CAN-mediated ring-opening of cyclopropyl sulfides
A facile method for synthesizing 3β-chlorinated 2,6-disubstituted tetrahydropyrans is described. Introduction of a chloride to 2β-substituted and 2β,4α-disubstituted 3-oxabicyclo[3.1.0]hexyl phenyl sulfides proceeded efficiently by a CAN-mediated oxidation to give 3β-chlorinated tetrahydropyrans ste...
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| Published in: | Tetrahedron letters Vol. 39; no. 41; pp. 7545 - 7548 |
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| Main Authors: | , , , , , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
Elsevier Ltd
08-10-1998
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| Online Access: | Get full text |
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| Summary: | A facile method for synthesizing 3β-chlorinated 2,6-disubstituted tetrahydropyrans is described. Introduction of a chloride to 2β-substituted and 2β,4α-disubstituted 3-oxabicyclo[3.1.0]hexyl phenyl sulfides proceeded efficiently by a CAN-mediated oxidation to give 3β-chlorinated tetrahydropyrans stereoselectively and in good yields, while the CAN-oxidation of 2β,4β-disubstituted 3-oxabicyclo[3.1.0]hexyl phenyl sulfide afforded the 3β-chlorinated tetraahydropyran as a minor product. However, by tuning the aryl group of the sulfide, the desired 2β,3β,6β-chlorinated product was obtained in good yield. The following silane-reduction of the bicyclic chlorinated acetal gave the cis-fused chlorinated bicyclic ether, where all substituents are oriented on the same side.
Cis-fused bicyclic ether with an axially oriented chlorine was synthesized from cyclopropyl sulfides by a CAN-promoted oxidation. |
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| ISSN: | 0040-4039 1873-3581 |
| DOI: | 10.1016/S0040-4039(98)01641-4 |