Abstract
Although C-H oxidation of hydrocarbons is generally difficult, allylic C-H oxidation is relatively simple and predictable, even on a preparative scale, because active species generated at the allylic position are stabilized by the double bond. Therefore, allylic oxidation has been employed in natural product synthesis, and a variety of reagents and conditions for allylic oxidation have been reported. However, reagents and conditions suitable for natural product synthesis are limited in terms of efficiency and chemo-, regio-, and stereoselectivity, owing to the structural and characteristic diversity of natural products. This review addresses allylic oxidations, highlighting reagents and conditions that meet the requirements for natural product synthesis. 1 Introduction 2 Selenium Reagents 2.1 Selenium Dioxide 2.2 Diphenyldiselenide-Iodoxybenzene 3 Chromium(VI) Reagents 3.1 Chromic Acid and Chromate Ester 3.2 Chromium Trioxide-3,5-Dimethylpyrazole (CrO 3·3,5-DMP) 3.3 PCC and PDC 4 Transition-Metal Reagents 5 Others 6 Conclusion.
| Original language | English |
|---|---|
| Article number | SS-2012-E0997-R |
| Pages (from-to) | 1421-1451 |
| Number of pages | 31 |
| Journal | Synthesis (Germany) |
| Volume | 45 |
| Issue number | 11 |
| DOIs | |
| Publication status | Published - 2013 May 15 |
Keywords
- C-H oxidation
- allylic oxidation
- natural products
- selectivity
- total synthesis
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry