3 years ago

Applications of the Wittig–Still Rearrangement in Organic Synthesis

Applications of the Wittig–Still Rearrangement in Organic Synthesis
Tomas Hudlicky, Lukas Rycek
This Review traces the discovery of the Wittig–Still rearrangement and its applications in organic synthesis. Its relationship to Wittig rearrangements is discussed along with detailed analysis of E/Z- and diastereoselectivity. Modifications of the products arising from the Wittig–Still rearrangement are reviewed in the context of increased complexity in intermediates potentially useful in target-oriented synthesis. Early applications of the Wittig–Still rearrangement to modifications of steroids are reviewed as are applications to various terpene and alkaloid natural product targets and miscellaneous compounds. To the best of our knowledge, the literature is covered through December 2016. A useful synthetic tool: The reaction today known as the Wittig–Still rearrangement was first described almost four decades ago. It provides distinct advantages summarized in this Review: It leads, in most cases, to selective preparation of Z-olefins, it is an excellent method for the construction of quaternary centers, and it proceeds with complete transfer of chirality.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201611329

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