Tetrahedron p. 6087 - 6104 (1992)
Update date:2022-09-26
Topics:
Louw, Jaap van der
Baan, Juul L. van der
Kanter, Franciscus J. J. de
Bickelhaupt, Friedrich
Klumpp, Gerhard W.
Reaction of 2-(bromozincmethyl)-2-alkenyl ethers 1 a,b,c,d with 1-(trimethylsilyl)-1-alkynes 2 afforded carbometallation products 3, which were converted by Pd(0)-catalyzed cyclization to 4-methylenecyclopentenes 5.The rates of both the addition and cyclization step depend on the concentration of the organozinc compound and the preparation of 5 is best performed using a 1,4-1,8 M solution of 1.At lower concentrations reaction times must be longer and, when 1c is reacted, the addition reaction is incomplete and gives rise to a mixture of products (3 and 14), which on Pd(0)-treatment leads to a mixture of isomeric methylenecyclopentenes (5, 15 and 16). - Key Words: alkyne addition; carbometallation; 2-alkenylzinc compounds; Pd(0)-catalysis; cyclopentenes.
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Doi:10.1021/ol401317m
(2013)Doi:10.1016/j.tetlet.2013.04.076
(2013)Doi:10.1039/c39920000563
(1992)Doi:10.1016/S0040-4020(01)88231-4
(1992)Doi:10.1134/S1070428013050229
()Doi:10.1016/S0040-4039(00)61146-2
(1992)
