244056-18-6Relevant articles and documents
One-pot method for regioselective bromination and sequential carbon-carbon bond-forming reactions of allylic alcohol derivatives
Kutsumura, Noriki,Matsubara, Yusuke,Niwa, Kentaro,Ito, Ai,Saito, Takao
, p. 3337 - 3346 (2013/06/27)
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
TBAF-promoted dehydrobrominations of vicinal dibromides having an adjacent O-functional group
Kutsumura, Noriki,Kubokawa, Keisuke,Saito, Takao
experimental part, p. 2717 - 2720 (2010/12/25)
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.
Efficient synthesis of propargylic ethers under the DBU conditions and its application to natural products synthesis
Yokoyama, Tadashi,Kutsumura, Noriki,Ohgiya, Tadaaki,Nishiyama, Shigeru
, p. 578 - 582 (2008/02/11)
Conversion of dibromides carrying O-functional groups at adjacent positions to the corresponding propargylic ethers was successfully carried out under the DBU conditions through 2-bromo-1-alkenes as intermediates. The optically active γ-lactone-class natural products, such as (-)-muricatacin (4) and (R,R)-sapinofuranone B (5) were synthesized using the propargylic ether intermediate produced by the elimination reaction mentioned above.