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Synlett 1997; 1997(12): 1393-1394
DOI: 10.1055/s-1997-1069
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Stereo- and Regioselective Bromination of 1,5-Cyclooctadiene Derivatives and Their Substitution Reactions with Organocopper Reagents

Yoshiyasu Baba, Carole Noutary, Satsuki Ichikawa, Tetsuo Kusumoto1 , Hisayuki Watanabe, Michiaki Adachi, Hiroyasu Hotta, Yasuyuki Nakajima2 , Kazutaka Arai, Tamejiro Hiyama3
  • 1Sagami Chemical Research Center, 4-4-1 Nishiohnuma, Sagamihara, Kanagawa 229, Japan
  • 2Central Research Institute, Nissan Chemical Industries, Ltd., 722-1 Tsuboicho, Funabashi, Chiba 274, Japan
  • 3Research Laboratory of Resources Utilization, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama, Kanagawa 226, Japan
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Publication Date:
31 December 2000 (online)

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Bromination of tetramethyl cyclooctadiene-1,2,5,6-tetracarboxylate with N-bromosuccinimide took place with high selectivity to give the corresponding 3,7-cis-dibromide, which allowed us to introduce two (the same or different) alkyl substituents at C(3) and C(7) with one-step or stepwise use of organocopper reagents.

eight-membered carbocycle - stereoselective bromination - organocopper reagent