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2004
Alkenes
Q 0083
45- 081
Ruthenium-Catalyzed Transformation of 3-Benzyl But-1-ynyl Ethers into
1,3-Dienes and Benzaldehyde via Transfer Hydrogen. — A new catalytic cleavage
of ethynyl benzyl ethers is presented, which provides access to conjugated dienes
(II)/(III) in moderate to good E-selectivity and benzaldehyde. This method is successfully applied to the ring opening of ethynyl-substituted cyclic ethers like tetrahydrofurans (VII) or hydrogenated pyran derivatives (IV) to give the corresponding dienones
in good yields and E-selectivities. The reaction mechanism is discussed and an atypical
pattern of transfer hydrogenation is proposed. — (YEH, K.-L.; LIU, B.; LAI, Y.-T.; LI,
C.-W.; LIU*, R.-S.; J. Org. Chem. 69 (2004) 14, 4692-4694; Dep. Chem., Natl. Tsing
Hua Univ., Hsinchu 30043, Taiwan; Eng.) — Mischke
2004
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