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ChemInform Abstract: Stereoselective Hydrogenolysis of 1,1-Dibromo-1-alkenes and Stereospecific Synthesis of Conjugated (Z)-Alkenyl Compounds.

✍ 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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✦ 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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