α-Hydroxylation of β-Dicarbonyl Compounds

✍ Scribed by Jens Christoffers; Angelika Baro; Thomas Werner

• Publisher: John Wiley and Sons
• Year: 2004
• Tongue: English
• Weight: 223 KB
• Volume: 346
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/adsc.200303140

✦ Synopsis

Abstract

The most convenient and direct route to α‐hydroxy‐β‐dicarbonyl compounds is the oxidation of readily accessible 1,3‐dicarbonyls. Hence, this type of oxidation is an intensively investigated field. In this short review, we present and compare α‐hydroxylations using various oxidants such as peracids (Rubottom oxidation), dimethyldioxirane or molecular oxygen. From an economical and ecological point of view, metal‐catalyzed air oxidations are optimal at least for cyclic β‐dicarbonyls. For asymmetric α‐hydroxylations only chiral sulfonyloxaziridines are available to date. Thus, there is still a need for significant development in this area.