Stereoselective nucleophilic substitution of 6-(tert-butyldimethylsilyloxy)-3,6-dihydro-2H-pyran-3-yl acetate: application to the synthesis of a NK1 receptor antagonist |
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| Authors: | Kazutoshi Sugawara Tomiki Hashiyama |
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| Affiliation: | Medicinal Chemistry Research Laboratories, Tanabe Seiyaku Co., Ltd, 2-2-50, Kawagishi, Toda-shi, Saitama 335-8505, Japan |
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| Abstract: | Reaction of chiral cis- and trans-6-(tert-butyldimethylsilyloxy)-3,6-dihydro-2H-pyran-3-yl acetates with various nucleophiles (allyltrimethylsilane, bistrimethylsilylacetylene, benzyl alcohol, benzyl carbamate etc.) in the presence of a Lewis acid gave the corresponding 2,3-unsaturated pyran derivatives in good to excellent yield with trans selectivity. Application to the synthesis of NK1 antagonist is also described. |
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