Unsaturated sulfoxides in organic synthesis: A new general furan synthesis

Wing Hong Chan; Albert W.M. Lee; Eddy T.T. Chan

doi:10.1039/p19920000945

Unsaturated sulfoxides in organic synthesis: A new general furan synthesis

Wing Hong Chan^*, Albert W.M. Lee, Eddy T.T. Chan

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

23 Citations (Scopus)

Abstract

Furans have been efficiently synthesised by a three-step reaction sequence. Michael addition of keto esters to alkenyl sulfoxides followed by Pummerer rearrangement afforded the cyclic intermediates 11 in good yield. Treatment of the latter with 2-chloroperoxybenzoic acid led by oxidation and syn-elimination of the corresponding sulfoxide, to substituted furans.

Original language	English
Pages (from-to)	945-946
Number of pages	2
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	8
DOIs	https://doi.org/10.1039/p19920000945
Publication status	Published - 1992

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title = "Unsaturated sulfoxides in organic synthesis: A new general furan synthesis",

abstract = "Furans have been efficiently synthesised by a three-step reaction sequence. Michael addition of keto esters to alkenyl sulfoxides followed by Pummerer rearrangement afforded the cyclic intermediates 11 in good yield. Treatment of the latter with 2-chloroperoxybenzoic acid led by oxidation and syn-elimination of the corresponding sulfoxide, to substituted furans.",

author = "Chan, {Wing Hong} and Lee, {Albert W.M.} and Chan, {Eddy T.T.}",

year = "1992",

doi = "10.1039/p19920000945",

language = "English",

pages = "945--946",

journal = "Journal of the Chemical Society, Perkin Transactions 1",

issn = "1472-7781",

publisher = "Chemical Society",

number = "8",

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TY - JOUR

T1 - Unsaturated sulfoxides in organic synthesis

T2 - A new general furan synthesis

AU - Chan, Wing Hong

AU - Lee, Albert W.M.

AU - Chan, Eddy T.T.

PY - 1992

Y1 - 1992

N2 - Furans have been efficiently synthesised by a three-step reaction sequence. Michael addition of keto esters to alkenyl sulfoxides followed by Pummerer rearrangement afforded the cyclic intermediates 11 in good yield. Treatment of the latter with 2-chloroperoxybenzoic acid led by oxidation and syn-elimination of the corresponding sulfoxide, to substituted furans.

AB - Furans have been efficiently synthesised by a three-step reaction sequence. Michael addition of keto esters to alkenyl sulfoxides followed by Pummerer rearrangement afforded the cyclic intermediates 11 in good yield. Treatment of the latter with 2-chloroperoxybenzoic acid led by oxidation and syn-elimination of the corresponding sulfoxide, to substituted furans.

UR - http://www.scopus.com/inward/record.url?scp=37049066879&partnerID=8YFLogxK

U2 - 10.1039/p19920000945

DO - 10.1039/p19920000945

M3 - Journal article

AN - SCOPUS:37049066879

SN - 1472-7781

SP - 945

EP - 946

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 8

ER -

Unsaturated sulfoxides in organic synthesis: A new general furan synthesis

Abstract

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