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Spiro[2.5]octa-4,7-dien-6-one

Base Information
  • Chemical Name:Spiro[2.5]octa-4,7-dien-6-one
  • CAS No.:766-35-8
  • Molecular Formula:C8H8O
  • Molecular Weight:120.151
  • Hs Code.:
Spiro[2.5]octa-4,7-dien-6-one

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Chemical Property of Spiro[2.5]octa-4,7-dien-6-one
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Refernces

Enantioselective Spirocyclopropanation of para-Quinone Methides Using Ammonium Ylides

10.1021/acs.orglett.7b00869

The study presents a highly enantioselective and broadly applicable method for spirocyclopropanation reactions of para-quinone methides using Cinchona alkaloid-based chiral ammonium ylides. The primary objective was to develop a straightforward protocol for synthesizing the chiral spiro[2.5]octa-4,7-dien-6-one skeleton, a structural motif prevalent in biologically active molecules. Key chemicals included para-quinone methides as acceptors for cyclopropanation reactions, quinone diazides, and ammonium ylides, particularly those derived from Cinchona alkaloids. These chemicals served to facilitate the formation of chiral spirocyclopropanes, which are valuable intermediates in the synthesis of complex pharmaceutical targets and possess pharmacological properties. The study optimized reaction conditions and identified the best-suited chiral amine leaving group, leading to high yields and excellent stereoselectivities in the synthesis of chiral spiro[2.5]octa-4,7-dien-6-ones.

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