ChemInform Abstract: Stereoselective Hydrogenolysis of 1,1-Dibromo-1-alkenes and Stereospecific Synthesis of Conjugated (Z)-Alkenyl Compounds.
β Scribed by Jun'ichi Uenishi; Reiko Kawahama; Osamu Yonemitsu; Jiro Tsuji
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 38 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0931-7597
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β¦ Synopsis
Stereoselective Hydrogenolysis of 1,1-Dibromo-1-alkenes and Stereospecific Synthesis of Conjugated (Z)-Alkenyl Compounds.
-The Pd-catalyzed hydrogenolysis of 1,1-dibromo-1-alkenes with Bu 3 SnH proceeds stereoselectively yielding (Z)-1-bromo-1-alkenes. Alkenyl-and alkynylconjugated 1,1-dibromo-1-alkenes also undergo stereoselective hydrogenolysis. The reaction of the 1,1-diiodoalkene (VI) gives a mixture of products, while 1,1-dichloro-1-alkenes do not react under these conditions.
Pd-catalyzed cross-couplings of 1,1-dibromo-1-alkenes and (Z)-1-bromo-1-alkenes provide polyenes or enynes bearing a (Z)-alkenyl unit in good yields. -(UENISHI, JUN'ICHI; KAWAHAMA, REIKO; YONEMITSU,
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