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Synlett 1997; 1997(8): 863-875
DOI: 10.1055/s-1997-925
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A Novel Domino Route to Chiral Cyclobutanones and its Function as Cornerstone in the Synthesis of Versatile Natural Products

Hideo Nemoto* , Keiichiro Fukumoto
  • *Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-77, Japan, FAX 022 217 6878
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Publication Date:
31 December 2000 (online)

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A novel enantiocontrolled method for the synthesis of chiral cyclobutanones is described. This consists of the preparation of chiral cyclopropanols using a chiral oxathiane as a chiral auxiliary followed by enantiospecific expansion of the cyclopropane ring, domino asymmetric epoxidation and enantiospecific ring expansion (DAE-ERE) of cyclopropylideneethanols, and asymmetric dihydroxylation of the cyclopropylidene group followed by enantiospecific expansion of the resulting cyclopropanediols. Ortho-substituents of the aromatic ring have particularly strong effects on enantioselectivity in the DAE-ERE reactions of aromatic cyclopropylideneethanols. The resulting cyclobutanones are very versatile building blocks, as shown in the enantiocontrolled synthesis of various types of compounds such as pheromones, terpenes, and alkaloids.

domino reaction - cyclopropylidene substituted alcohol - oxaspiropentane - chiral cyclobutanone - natural product synthesis