Asymmetric spirocyclization: A new type of acid-catalyzed intramolecular 1,4-addition to form carba-spirocyclic compounds

Satoshi Yamada, Satoru Karasawa, Youichi Takahashi, Mariko Aso, Hiroshi Suemune

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Novel spirocyclization based on intramolecular 1,4-addition and its asymmetric version have been developed using a combination of Lewis acid and 1,2-diol. Treatment of five- and six-membered α,β-unsaturated cyclic ketones having a 4-oxopentyl group at the β-position with Lewis acid and ethylene glycol gave spiro[4.5]decane-2,7-dione and spiro[5.5]undecane-2,8- done, respectively. The asymmetric version of this reaction has been developed by using optically active 1,2-diol such as cyclohexane-1,2-diol to afford the spirocyclic products of up to 85% e.e.

Original languageEnglish
Pages (from-to)15555-15566
Number of pages12
JournalTetrahedron
Volume54
Issue number51
DOIs
Publication statusPublished - Dec 17 1998

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Lewis Acids
Acids
Ethylene Glycol
Ketones
Cyclohexane
undecane
decane

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Asymmetric spirocyclization : A new type of acid-catalyzed intramolecular 1,4-addition to form carba-spirocyclic compounds. / Yamada, Satoshi; Karasawa, Satoru; Takahashi, Youichi; Aso, Mariko; Suemune, Hiroshi.

In: Tetrahedron, Vol. 54, No. 51, 17.12.1998, p. 15555-15566.

Research output: Contribution to journalArticle

Yamada, Satoshi ; Karasawa, Satoru ; Takahashi, Youichi ; Aso, Mariko ; Suemune, Hiroshi. / Asymmetric spirocyclization : A new type of acid-catalyzed intramolecular 1,4-addition to form carba-spirocyclic compounds. In: Tetrahedron. 1998 ; Vol. 54, No. 51. pp. 15555-15566.
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