α-Hydroxydimethylacetal formation from aminoketones using hypervalent iodine

✍ Scribed by Robert M. Moriarty; Om Prakash; Pauline Karalis; Indra Prakash

• Book ID: 104233873
• Publisher: Elsevier Science
• Year: 1984
• Tongue: French
• Weight: 183 KB
• Volume: 25
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)81508-2

✦ Synopsis

Various B-aminoketones were converted into the a-hydroxydimethylacetal using either o-iodosylbenzoic acid or (diacetoxy) iodobenzene (KOH/CHROH) without oxidation at lo, 2' or 3", amino groups or at sulfur in the case of a morpholino group.

We have demonstrated the usefulness of C~H.$(OAC)~ in methanolic base for the conversion of enolizable carbonyl compounds into a-hydroxydimethylacetals.1-5 As with any oxidative procedure in organic synthesis, the compatibility of other potentially oxidizable func-