Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
5 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

You might also like
Discover & Discuss Important Research

Keeping up-to-date with research can feel impossible, with papers being published faster than you'll ever be able to read them. That's where Researcher comes in: we're simplifying discovery and making important discussions happen. With over 19,000 sources, including peer-reviewed journals, preprints, blogs, universities, podcasts and Live events across 10 research areas, you'll never miss what's important to you. It's like social media, but better. Oh, and we should mention - it's free.

  • Download from Google Play
  • Download from App Store
  • Download from AppInChina

Researcher displays publicly available abstracts and doesn’t host any full article content. If the content is open access, we will direct clicks from the abstracts to the publisher website and display the PDF copy on our platform. Clicks to view the full text will be directed to the publisher website, where only users with subscriptions or access through their institution are able to view the full article.