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2005
Ring closure reactions
O 0130
Ruthenium-Catalyzed Enyne Cycloisomerizations. Effect of Allylic Silyl Ether on
— The ruthenium-catalyzed cycloisomerization of 1,6- and
15- 040 Regioselectivity.
1,7-enynes such as (III), (V), (VIII) or (XIV) substituted in the terminal allylic position
with a Tbs ether group emerges as an effective reaction to form unprecedented fiveand six-membered rings possessing a geometrically defined enol silane. The level of
selectivity is shown to depend on the alkyne substitution, the geometry of the allylic
double bond and the nature of the catalyst. The reactions can be carried out under mild
conditions in acetone at room temperature. The reversal of the polarity such as in
(XVII) serves as a convenient entry into α-methylene-δ-butyrolactones. Examples of
stereoinduction are shown. — (TROST*, B. M.; SURIVET, J.-P.; TOSTE, F. D.; J.
Am. Chem. Soc. 126 (2004) 47, 15592-15602; Dep. Chem., Stanford Univ., Stanford,
CA 94305, USA; Eng.) — Kieslich
2005
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