Unusual Stereoselectivity in Elimination Reactions of Allylic Acetate Catalyzed by Pd(PPh3)4 in (±)-9α,11α,15α-triacetate Cloprostenol p-Methoxybenzyl Ester

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Abstract

Attempts to replace the allylic C15-acetate group of cloprostenol with a tosyl group under phase-transfer catalysis conditions (СH2Cl2/H2O, R3R′N+Hal-, NaOH, TsOH, Pd(PPh3)4) led to the corresponding 13E, 15Z derivative with moderate yield. The same compound is stereoselectivity formed in high yield when this reaction is carried out in a THF-Pd(PPh3)4-NaH medium.

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About the authors

V. V. Zagitov

Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences

Email: vostrikov@anrb.ru
Russian Federation, prosp. Oktyabrya, 71, Ufa, 450054

N. S. Vostrikov

Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences

Author for correspondence.
Email: vostrikov@anrb.ru
prosp. Oktyabrya, 71, Ufa, 450054

M. S. Miftakhov

Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences

Email: vostrikov@anrb.ru
Russian Federation, prosp. Oktyabrya, 71, Ufa, 450054

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2. Scheme 1. Key stage of transformation of the initial block 2.

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3. Scheme 2. Stages of obtaining key block 2.

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