- Conversion of 3-O-substituted 1,2-dibromoalkanes into 2-bromo-1-alkenes by the selective elimination: Its application to total synthesis of 12-oxygenated tremetones
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2-Bromo-1-alkenes were efficiently synthesized in good yields by the regioselective HBr-elimination reaction of 3-aryloxy- or 3-acyloxy-1,2- dibromoalkanes. Total synthesis of several oxygenated tremetones has been accomplished by using the 2-bromo-1-alkene derivative produced by this elimination reaction.
- Ohgiya, Tadaaki,Nishiyama, Shigeru
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Read Online
- One-pot method for regioselective bromination and sequential carbon-carbon bond-forming reactions of allylic alcohol derivatives
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An efficient one-pot method for the regioselective bromination of allylic alcohol derivatives (two-step reaction sequence) followed by Sonogashira, Negishi, or Suzuki-Miyaura coupling reactions in the same reaction vessel (three-step reaction sequence) ha
- Kutsumura, Noriki,Matsubara, Yusuke,Niwa, Kentaro,Ito, Ai,Saito, Takao
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p. 3337 - 3346
(2013/06/27)
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- TBAF-promoted elimination of vicinal dibromides having an adjacent O-functional group: Syntheses of 2-bromoalk-1-enes and alkynes
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Syntheses of 2-bromoalk-1-enes and alkynes were achieved in good yields by dehydrobromination of vicinal dibromides with tetrabutylammonium fluoride. Neighboring O-functional-group participation is important in determining elimination reactivity. Georg Thieme Verlag Stuttgart New York.
- Kutsumura, Noriki,Kubokawa, Keisuke,Saito, Takao
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experimental part
p. 2377 - 2382
(2011/09/16)
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- Novel one-pot method for chemoselective bromination and sequential sonogashira coupling
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(Equation Presented). An efficient one-pot method for bromination- elimination of allyl alcohol derivatives and sequential Sonogashira coupling has been developed. A highlight of the method is chemoselective DBU-promoted elimination of vicinal dibromoalka
- Kutsumura, Noriki,Niwa, Kentaro,Saito, Takao
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supporting information; experimental part
p. 3316 - 3319
(2010/10/19)
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- TBAF-promoted dehydrobrominations of vicinal dibromides having an adjacent O-functional group
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Regioselective HBr elimination of vicinal dibromides having an adjacent oxygen functional group to give the corresponding 2-bromoalk-1-enes was controlled using 1.1 equivalents of TBAF. Two-step elimination to give the corresponding alkynes was controlled using 5.0 equivalents of TBAF. High yield and high selectivity require the presence of an oxygen functional group at the neighboring position of the elimination site.
- Kutsumura, Noriki,Kubokawa, Keisuke,Saito, Takao
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experimental part
p. 2717 - 2720
(2010/12/25)
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- The synthesis of ethanolamine libraries from olefin scaffolds
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A solution-phase, multi-reaction sequence has been developed for the parallel synthesis of ethanolamine libraries. This approach uses 2,3-dibromopropene as a template for the synthesis of a small olefin sub-library, which is then further functionalized to
- Organ,Kaldor,Dixon,Parks,Singh,Lavorato,Isbester,Siegel
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p. 8407 - 8411
(2007/10/03)
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- Neighbouring-group influence on the ring opening of 2-aryloxymethyl-1,1,2-tribromocyclopropanes under phase-transfer conditions
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When a number of 2-aryloxymethyl-1,1,2-tribromocyclopropanes were treated with sodium hydroxide and ethanol under phase-transfer conditions, ring opening occurred to give mixtures of acetylenic diethyl acetals and ketals in better than 80% total isolated yield. The acetylenic diethyl ketals predominated significantly and were, in some cases, almost the exclusive product. It is argued that this ketal selectivity is in part caused by hydrogen bonding between ethanol and the aryloxy group.
- Bakstad, Einar,Olsen, Are S.,Sandberg, Marcel,Sydnes, Leiv K.
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p. 465 - 472
(2007/10/03)
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