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2004
Ring closure reactions
O 0130
Ni-Catalyzed, ZnCl2-Assisted Domino Coupling of Enones, Alkynes, and Alkenes.
A Ni(0)/ZnCl2 system effectively promotes the coupling of enones and alkene-teth51- 036 —
ered alkynes affording the corresponding coupling products with high regio- and
stereoselectivity. The geometry of the products is governed by the structure of the starting enynes and also by the reaction medium, with or without Et3N and/or PPh3. Alkynes
with a gem-disubstituted alkene part undergo the insertion of a second alkene unit to
cause a domino effect via a three-fold C—C bond formation process with and without
the cleavage of one C—C bond. Thus, the cyclopentene (XIX) bearing an alkynyl and
an alkenyl moiety reacts with (V) to give a triquinane-type product (XX) in a highly
stereoselective mode. — (IKEDA*, S.-I.; SANUKI, R.; MIYACHI, H.; MIYASHITA,
H.; TANIGUCHI, M.; ODASHIMA, K.; J. Am. Chem. Soc. 126 (2004) 33,
10331-10338; Grad. Sch. Pharm. Sci., Nagoya City Univ., Mizuho, Nagoya 467, Japan;
Eng.) — Bartels
2004
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