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2005
Pyran derivatives
R 0340
Regioselectivity Control in a Ruthenium-Catalyzed Cycloisomerization of
— The diyne-ols containing an alkynylsilane undergo cycloisomerization
10- 137 Diyne-ols.
in the presence of the cationic ruthenium complex RAC to form 2-silyl-[6H]-pyrans or
isomeric dihydropyrans. The regioselectivity of the reaction is controlled by substrate
design (presence/absence of a heteroatom in the tether) or by solvent selection. Fiveand six-membered rings are formed, although cyclization to a five-membered ring is
much more facile. Substrates bearing tertiary propargylic and secondary benzylic alcohols participate more readily than simple secondary ones. — (TROST*, B. M.;
RUDD, M. T.; COSTA, M. G.; LEE, P. I.; POMERANTZ, A. E.; Org. Lett. 6 (2004)
23, 4235-4238; Dep. Chem., Stanford Univ., Stanford, CA 94305, USA; Eng.) —
Steudel
2005
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