Modern Cyclopropanation via Non‐Traditional Building Blocks

Author:

Kelly Christopher B.1ORCID,Thai‐Savard Léa2ORCID,Hu Jiefeng3ORCID,Marder Todd B.4ORCID,Molander Gary A.56ORCID,Charette André B.7ORCID

Affiliation:

1. Discovery Process Research Janssen Research & Development LLC 1400 McKean Road Spring House PA 19477 USA

2. Discovery Chemistry Genentech, Inc. South San Francisco CA 94080 USA

3. Electronics and Information Displays & College of Chemistry and Life Sciences Nanjing University of Posts & Telecommunications 9 Wenyuan Road Nanjing 210023 China

4. Institut für Anorganische Chemie and Institute for Sustainable Chemistry & Catalysis with Boron Julius-Maximilians-Universität Würzburg Am Hubland 97074 Würzburg Germany

5. Department of Chemistry University of Pennsylvania Philadelphia PA, 19104 USA

6. Université Paris – Saclay Gif-sur-Yvette 91190 France

7. FRQNT Centre in Green Chemistry and Catalysis, Department of Chemistry Université de Montréal 1375 av. Thérèse Lavoie-Roux Montréal QC H2V 0B3 Canada

Abstract

AbstractSmall, strained carbocyclic systems have fascinated organic chemists from both a theoretical and synthetic standpoint. These systems often challenge conventional wisdom when it comes to molecular structure and tactics for chemical construction. The cyclopropyl motif is one such ring system that remains at the forefront of method development in the modern era. With the advent of an array of non‐traditional building blocks, a range of new cyclopropanation processes using one‐ and two‐electron strategies have been developed that not only overcome the synthetic shortcomings of classical approaches but also provide entry into a wide range of new classes of cyclopropanes. This review discusses recent advances in this area with an emphasis on their mechanistic underpinnings and potential applications. Additionally, a concise overview of the properties of and traditional approaches to cyclopropanes is provided.

Publisher

Wiley

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