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Synthesis of syn and anti 1,4-Diols by Copper-Catalyzed Boration of Allylic Epoxides

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  • Dr. Mariola Tortosa

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    1. Departamento de Química Orgánica (Módulo 01), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid (Spain), Fax: (+34) 91-497-466
    • Departamento de Química Orgánica (Módulo 01), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid (Spain), Fax: (+34) 91-497-466===

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  • This work was performed at the Instituto de Química Orgánica (CSIC) in Madrid. The author is indebted to Dr. Roberto Fernández de la Pradilla and Dr. Alma Viso for their generous support [MICINN (CTQ2009-07752) and CM (S-SAL-02449-2006)] and guidance. The author also thanks MCI for Juan de la Cierva and Ramón y Cajal contracts and CSIC for a JAE contract. The assistance of students Ignacio Colomer and Carlos Reviejo in the preparation of allylic epoxides 12 and 14 is also appreciated.

Abstract

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Mit- oder gegeneinander? Syn- und anti-1,4-Diole wurden durch regio- und diastereoselektive CuI-katalysierte Borierung von Allylepoxiden hergestellt (siehe Schema; pin=Pinakolato, TES=Triethylsilyl). Dabei ließen sich im ersten Schritt einfach geschützte 1,4-Diole durch eine Eintopfsequenz aus Addition, Schützung und Oxidation erhalten.

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