Lewis acid catalyzed ring opening reaction of cyclobutane-1,2-diols having 1-alkoxyalkyl substituents. Selective synthesis of α,α-disubstituted β-hydroxycyclopentanones

✍ Scribed by Isao Kuwajima; Ichiro Azegami

• Publisher: Elsevier Science
• Year: 1979
• Tongue: French
• Weight: 200 KB
• Volume: 20
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)93976-0

✦ Synopsis

On treating with stannic chloride, silyl ethers of cyclobutane-1,2-diols having 1-alkoxyalkyl substituents at l-position undergo a facile ring opening reaction to afford the corresponding B-hydroxycyclopentanones or 1,4-diketones in good yield. Cyclobutanone derivatives have frequently been employed as versatile synthetic intermediates. 1 For example, such kind of compounds possessing appropriate substituents are shown to undergo a facile ring opening reaction under basic conditions to afford various synthetically useful materials. 2 Recently, we have described a synthetic utility of 1,2-bis(trimethylsiloxy)-1-cyclobutene for the preparation of cyclobutanone derivatives and have shown that 2-trimethylsiloxy-2-(l-alkoxyalkyl)cyclobutanones l_, prepared easily from the reaction of the cyclobutene with acetals, undergo ring cleavage to yield the corresponding rearrangement products 2, 3 2-substituted cyclopentane-1,3-diones, or ring opening ones 2, 4 silyl en01 ethers of y-keto esters, selectively upon treating with trifluoroacetic acid or stannic chloride, respectively.