Tetrahedron Letters

Catalytic isomerization of acetylenic silyl ethers to dienol silyl ethers by ruthenium hydride complexes

K Hirai, H Suzuki, Y Moro-Oka, T Ikawa

Index: Hirai, Kenji; Suzuki, Hiroharu; Moro-oka, Yoshihiko; Ikawa, Tsuneo Tetrahedron Letters, 1980 , vol. 21, p. 3413 - 3416

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Citation Number: 34

Abstract

2a; Mixture of (Z,Z) and (Z,E) stero isomers. (Z,Z)/(Z,E) = 1 : 1 based on the 1 H nmr spectroscopy. 1 H nmr (CCl 4 , TMS); (Z,Z) isomer, δ 0.12(s, 18H), 5.34 (dd, J=4, 1Hz, 2H), 5.88 (dd, J=4, 1Hz, 2H). (Z,E) isomer, 0.12 (s, 18H), 4.77 (d, H d , J dc =5Hz), 4.94 (d, H c , J cd =5Hz), 5.17 (d, H a , J ab =12Hz), 6.44 (d, H b , J ba =12Hz). ... Formation of (Z,Z) and (Z,E) isomers of 2a is explained by a stereoselective addition of ruthenium hydride to the allene ...