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Palladium-catalyzed allylation of lithium 3-alkenyl-1-cyclopentenolates-triethylborane and its application to a selective synthesis of methyl (z)-jasmonate1

✍ Scribed by Fen-Tair Luo; Ei-ichi Negishi


Book ID
104229107
Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
280 KB
Volume
26
Category
Article
ISSN
0040-4039

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✦ Synopsis


A Pd-catalyzed allylation of 3-substituted 1-cyclopentenolates with readily obtainable and storable v-monosubstituted (Z)-allylic acetates in a 1:l ratio in the presence of 2 mol % of Pd(PPh3)4 featuring high yields and high stereo-and regioselectivities has been developed and applied to the synthesis of methyl (z)-jasmonate. The reaction of a 2:l mixture of BEt3 and a lithium 3-alkenyl-1-cyclopentenolate (l),