Rh(I)-Catalyzed 1,4-Conjugate Addition of Alkenylboronic Acids to a Cyclopentenone Useful for the Synthesis of Prostaglandins

Jin Fong Syu, Yun Ting Wang, Kung Cheng Liu, Ping Yu Wu, Julian P. Henschke, Hsyueh Liang Wu

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8 Citations (Scopus)

Abstract

An efficient and trans-diastereoselective Rh(I)-catalyzed 1,4-conjugate addition reaction of alkenylboronic acids and a homochiral (R)-4-silyloxycyclopentenone useful for the synthesis of derivatives of prostaglandins E and F is described for the first time. The reaction functions under mild conditions and is particularly rapid (≤6 h) under low power (50 W) microwave irradiation at 30 °C in MeOH in the presence of a catalytic amount of KOH. Under these conditions, 3 mol % of [RhCl(COD)]2 is typically required to produce high yields. The method also functions without microwave irradiation at 3 °C in the presence of a stoichiometric amount of KOH. Under these conditions, only 1.5 mol % of [RhCl(COD)]2 is needed, but the reaction is considerably slower. The method accepts a range of aryl- and alkyl-substituted alkenylboronic acids, and its utility has been demonstrated by the synthesis of PGF (dinoprost) and tafluprost.

Original languageEnglish
Pages (from-to)10832-10844
Number of pages13
JournalJournal of Organic Chemistry
Volume81
Issue number22
DOIs
Publication statusPublished - 2016 Nov 18

ASJC Scopus subject areas

  • Organic Chemistry

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