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Org Lett. 2010 Sep 3;12(17):3960-2. doi: 10.1021/ol101653b.

Titanium(IV) chloride-mediated carbon-carbon bond-forming reaction between 3,3-dialkylcyclobutanones and aldehydes.

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1
School of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan. jimatsuo@p.kanazawa-u.ac.jp

Abstract

Treatment of 3,3-dialkylcyclobutanones with titanium(IV) chloride in the presence of aldehyde gave beta'-chloro-beta-hydroxy ketones in high yields. It was speculated that ring cleavage of the cyclobutanone ring with titanium(IV) chloride gave trichlorotitanium enolate having a tertiary alkyl chloride moiety and then aldol reaction of the titanium enolate proceeded. A trialkylsilylmethyl group at the 2-position of cyclobutanone facilitated the ring cleavage. Synthesis of substituted cyclopentenone from an obtained product is also described.

PMID:
20690661
DOI:
10.1021/ol101653b
[Indexed for MEDLINE]
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