| Autor: |
Radhoff, Niklas, Daniliuc, Constantin G., Studer, Armido |
| Předmět: |
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| Zdroj: |
Angewandte Chemie International Edition; 8/21/2023, Vol. 62 Issue 34, p1-6, 6p |
| Abstrakt: |
Design, synthesis and application of benzene bioisosteres have attracted a lot of attention in the past 20 years. Recently, bicyclo[2.1.1]hexanes have emerged as highly attractive bioisosteres for ortho‐ and meta‐substituted benzenes. Herein we report a mild, scalable and transition‐metal‐free protocol for the construction of highly substituted bicyclo[2.1.1]hexan‐2‐ones through Lewis acid catalyzed (3+2)‐cycloaddition of bicyclo[1.1.0]‐butane ketones with disubstituted ketenes. The reaction shows high functional group tolerance as documented by the successful preparation of various 3‐alkyl‐3‐aryl as well as 3,3‐bisalkyl bicyclo[2.1.1]hexan‐2‐ones (26 examples, up to 89 % yield). Postfunctionalization of the exocyclic ketone moiety is also demonstrated. [ABSTRACT FROM AUTHOR] |
| Databáze: |
Complementary Index |
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