1-Lithio-2,2-diphenoxy-1-(phenylsulfonyl)cyclopropane as β-lithio acrylate and cyclopropanone acetal anion synthons.
1-Lithio-2,2-diphenoxy-1-(phenylsulfonyl)cyclopropane (4) reacted with alkyl halides to give the alkylated cyclopropyl sulfones 6, which were subjected to hydrolysis with TiCl4in CH2Cl2followed by elimination of the phenylsulfonyl group with DBU to afford α,β-unsaturated esters 8 and small amount of...
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| Main Authors: | , |
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| Format: | Article |
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2018
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| Online Access: | https://repository.li.mahidol.ac.th/handle/123456789/22542 |
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| Institution: | Mahidol University |
| Summary: | 1-Lithio-2,2-diphenoxy-1-(phenylsulfonyl)cyclopropane (4) reacted with alkyl halides to give the alkylated cyclopropyl sulfones 6, which were subjected to hydrolysis with TiCl4in CH2Cl2followed by elimination of the phenylsulfonyl group with DBU to afford α,β-unsaturated esters 8 and small amount of β,γ-unsaturated esters 9. Furthermore, reductive removal of the phenylsulfonyl group of compound 6 by using 6% Na-Hg furnished 2-alkyl substituted cyclopropanone acetals 12 in good yields. © 1993. |
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