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 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: Manat Pohmakotr, Jantima Ratchataphusit
Other Authors: Mahidol University
Format: Article
Published: 2018
Subjects:
Biochemistry, Genetics and Molecular Biology
Chemistry
Pharmacology, Toxicology and Pharmaceutics
Online Access:https://repository.li.mahidol.ac.th/handle/123456789/22542
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spelling th-mahidol.225422018-08-10T16:01:16Z 1-Lithio-2,2-diphenoxy-1-(phenylsulfonyl)cyclopropane as β-lithio acrylate and cyclopropanone acetal anion synthons. Manat Pohmakotr Jantima Ratchataphusit Mahidol University Biochemistry, Genetics and Molecular Biology Chemistry Pharmacology, Toxicology and Pharmaceutics 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. 2018-08-10T08:54:16Z 2018-08-10T08:54:16Z 1993-01-01 Article Tetrahedron. Vol.49, No.29 (1993), 6473-6482 10.1016/S0040-4020(01)80161-7 00404020 2-s2.0-0027328990 https://repository.li.mahidol.ac.th/handle/123456789/22542 Mahidol University SCOPUS https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=0027328990&origin=inward
institution Mahidol University
building Mahidol University Library
continent Asia
country Thailand
Thailand
content_provider Mahidol University Library
collection Mahidol University Institutional Repository
topic Biochemistry, Genetics and Molecular Biology
Chemistry
Pharmacology, Toxicology and Pharmaceutics
spellingShingle Biochemistry, Genetics and Molecular Biology
Chemistry
Pharmacology, Toxicology and Pharmaceutics
Manat Pohmakotr
Jantima Ratchataphusit
1-Lithio-2,2-diphenoxy-1-(phenylsulfonyl)cyclopropane as β-lithio acrylate and cyclopropanone acetal anion synthons.
description 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.
author2 Mahidol University
author_facet Mahidol University
Manat Pohmakotr
Jantima Ratchataphusit
format Article
author Manat Pohmakotr
Jantima Ratchataphusit
author_sort Manat Pohmakotr
title 1-Lithio-2,2-diphenoxy-1-(phenylsulfonyl)cyclopropane as β-lithio acrylate and cyclopropanone acetal anion synthons.
title_short 1-Lithio-2,2-diphenoxy-1-(phenylsulfonyl)cyclopropane as β-lithio acrylate and cyclopropanone acetal anion synthons.
title_full 1-Lithio-2,2-diphenoxy-1-(phenylsulfonyl)cyclopropane as β-lithio acrylate and cyclopropanone acetal anion synthons.
title_fullStr 1-Lithio-2,2-diphenoxy-1-(phenylsulfonyl)cyclopropane as β-lithio acrylate and cyclopropanone acetal anion synthons.
title_full_unstemmed 1-Lithio-2,2-diphenoxy-1-(phenylsulfonyl)cyclopropane as β-lithio acrylate and cyclopropanone acetal anion synthons.
title_sort 1-lithio-2,2-diphenoxy-1-(phenylsulfonyl)cyclopropane as β-lithio acrylate and cyclopropanone acetal anion synthons.
publishDate 2018
url https://repository.li.mahidol.ac.th/handle/123456789/22542
_version_ 1763497571243786240

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