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Addition and in situ halo-cyclization of -alkenyl Grignard reagents with aldehydes, ketones, carbon dioxide, and azodicarboxylate

An addition reaction of -alkenylmagnesium bromide with aldehydes and consecutive oxidative cyclization with iodobenzene diacetate afforded brominated tetrahydrofuran in one pot. The reaction was also applicable to a one-pot synthesis of 2,5,5-trisubstituted tetrahydrofuran, lactone, and pyrazolidine... Full description

Journal Title: New Journal of Chemistry 2013, Vol.37(12), pp.3873-3876
Main Author: Yamamoto, Yasutomo
Other Authors: Shimizu, Misa , Ohara, Ai , Miyawaki, Akari , Tomioka, Kiyoshi
Format: Electronic Article Electronic Article
Language:
ID: ISSN: 1144-0546 ; E-ISSN: 1369-9261 ; DOI: 10.1039/c3nj00765k
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recordid: rscc3nj00765k
title: Addition and in situ halo-cyclization of -alkenyl Grignard reagents with aldehydes, ketones, carbon dioxide, and azodicarboxylate
format: Article
creator:
  • Yamamoto, Yasutomo
  • Shimizu, Misa
  • Ohara, Ai
  • Miyawaki, Akari
  • Tomioka, Kiyoshi
ispartof: New Journal of Chemistry, 2013, Vol.37(12), pp.3873-3876
description: An addition reaction of -alkenylmagnesium bromide with aldehydes and consecutive oxidative cyclization with iodobenzene diacetate afforded brominated tetrahydrofuran in one pot. The reaction was also applicable to a one-pot synthesis of 2,5,5-trisubstituted tetrahydrofuran, lactone, and pyrazolidine using a ketone, carbon dioxide, and azodicarboxylate, respectively, as electrophiles. One-pot iodo- and chloro-cyclizations were also possible with alkenylmagnesium iodide and chloride.
language:
source:
identifier: ISSN: 1144-0546 ; E-ISSN: 1369-9261 ; DOI: 10.1039/c3nj00765k
fulltext: fulltext
issn:
  • 1144-0546
  • 1369-9261
  • 13699261
  • 11440546
url: Link


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titleAddition and in situ halo-cyclization of -alkenyl Grignard reagents with aldehydes, ketones, carbon dioxide, and azodicarboxylate
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descriptionAn addition reaction of -alkenylmagnesium bromide with aldehydes and consecutive oxidative cyclization with iodobenzene diacetate afforded brominated tetrahydrofuran in one pot. The reaction was also applicable to a one-pot synthesis of 2,5,5-trisubstituted tetrahydrofuran, lactone, and pyrazolidine using a ketone, carbon dioxide, and azodicarboxylate, respectively, as electrophiles. One-pot iodo- and chloro-cyclizations were also possible with alkenylmagnesium iodide and chloride.
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titleAddition and in situ halo-cyclization of -alkenyl Grignard reagents with aldehydes, ketones, carbon dioxide, and azodicarboxylate
descriptionAn addition reaction of -alkenylmagnesium bromide with aldehydes and consecutive oxidative cyclization with iodobenzene diacetate afforded brominated tetrahydrofuran in one pot. The reaction was also applicable to a one-pot synthesis of 2,5,5-trisubstituted tetrahydrofuran, lactone, and pyrazolidine using a ketone, carbon dioxide, and azodicarboxylate, respectively, as electrophiles. One-pot iodo- and chloro-cyclizations were also possible with alkenylmagnesium iodide and chloride.
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titleAddition and in situ halo-cyclization of -alkenyl Grignard reagents with aldehydes, ketones, carbon dioxide, and azodicarboxylate
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abstractAn addition reaction of -alkenylmagnesium bromide with aldehydes and consecutive oxidative cyclization with iodobenzene diacetate afforded brominated tetrahydrofuran in one pot. The reaction was also applicable to a one-pot synthesis of 2,5,5-trisubstituted tetrahydrofuran, lactone, and pyrazolidine using a ketone, carbon dioxide, and azodicarboxylate, respectively, as electrophiles. One-pot iodo- and chloro-cyclizations were also possible with alkenylmagnesium iodide and chloride.
doi10.1039/c3nj00765k
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date2013-11-11
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