ChemInform Abstract: Stereoselective Synthesis of β-Hydroxycyclohexanones.

✍ Scribed by A. P. RUTHERFORD; C. S. GIBB; R. C. HARTLEY

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 34 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199823083

✦ Synopsis

Stereoselective Synthesis of β-Hydroxycyclohexanones.

-A stereoselective route to β-hydroxycyclohexanones is reported. Thus Takai alkylidenation of the aldol (I) followed by desilylation and a novel anionic oxy-Cope rearrangement provides an enolate which undergoes 6-(enolendo)-exo-trig cyclization on acidic treatment to yield the 3,5-anti-substituted cyclohexanones (V) and (VII) preferentially. Interestingly, anionic oxy-Cope rearrangement of phenyl enol ether (X) under the same conditions allows the isolation of the aldehyde (XI) after mild neutral work-up. -(RUTHERFORD, A.