Model studies of the overall 5-endo-trig iodocyclization of homoallylic alcohols

Simon B. Bedford; Kathryn E. Bell; Frank Bennett; Christopher J. Hayes; David W. Knight; Duncan E. Shaw

doi:10.1039/A902411E

Model studies of the overall 5-endo-trig iodocyclization of homoallylic alcohols

Simon B. Bedford, Kathryn E. Bell, Frank Bennett, Christopher J. Hayes, David W. Knight, Duncan E. Shaw

Western Sydney University

Research output: Contribution to journal › Article › peer-review

50 Citations (Scopus)

Abstract

Overall 5-endo-trig iodocyclizations of homoallylic alcohols, with a range of substitution patterns, leading to Î²-iodotetrahydrofurans are usually highly efficient and stereoselective when carried out in anhydrous acetonitrile in the presence of sodium hydrogen carbonate. Such cyclizations, which are not exceptions to Baldwin's rules as they are electrophile-driven, appear to proceed via a well-ordered chair-like transition state. The iodine can be replaced by hydroxy, acetoxy and azide groups.

Original language	English
Pages (from-to)	2143-2153
Number of pages	11
Journal	Journal of the Chemical Society. Perkin Transactions 1
Volume	15
DOIs	https://doi.org/10.1039/A902411E
Publication status	Published - 1999

Keywords

allyl alcohol

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10.1039/A902411E

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abstract = "Overall 5-endo-trig iodocyclizations of homoallylic alcohols, with a range of substitution patterns, leading to {\^I}²-iodotetrahydrofurans are usually highly efficient and stereoselective when carried out in anhydrous acetonitrile in the presence of sodium hydrogen carbonate. Such cyclizations, which are not exceptions to Baldwin's rules as they are electrophile-driven, appear to proceed via a well-ordered chair-like transition state. The iodine can be replaced by hydroxy, acetoxy and azide groups.",

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AU - Bell, Kathryn E.

AU - Bennett, Frank

AU - Hayes, Christopher J.

AU - Knight, David W.

AU - Shaw, Duncan E.

PY - 1999

Y1 - 1999

N2 - Overall 5-endo-trig iodocyclizations of homoallylic alcohols, with a range of substitution patterns, leading to Î²-iodotetrahydrofurans are usually highly efficient and stereoselective when carried out in anhydrous acetonitrile in the presence of sodium hydrogen carbonate. Such cyclizations, which are not exceptions to Baldwin's rules as they are electrophile-driven, appear to proceed via a well-ordered chair-like transition state. The iodine can be replaced by hydroxy, acetoxy and azide groups.

AB - Overall 5-endo-trig iodocyclizations of homoallylic alcohols, with a range of substitution patterns, leading to Î²-iodotetrahydrofurans are usually highly efficient and stereoselective when carried out in anhydrous acetonitrile in the presence of sodium hydrogen carbonate. Such cyclizations, which are not exceptions to Baldwin's rules as they are electrophile-driven, appear to proceed via a well-ordered chair-like transition state. The iodine can be replaced by hydroxy, acetoxy and azide groups.

KW - allyl alcohol

UR - http://handle.westernsydney.edu.au:8081/1959.7/uws:47673

U2 - 10.1039/A902411E

DO - 10.1039/A902411E

M3 - Article

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VL - 15

SP - 2143

EP - 2153

JO - Journal of the Chemical Society. Perkin Transactions 1

JF - Journal of the Chemical Society. Perkin Transactions 1

ER -

Model studies of the overall 5-endo-trig iodocyclization of homoallylic alcohols

Abstract

Keywords

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