Enantioselective enol lactone synthesis under double catalytic conditions

Kennosuke Itoh, Masayuki Hasegawa, Junji Tanaka, Shuji Kanemasa

Research output: Contribution to journalArticle

85 Citations (Scopus)

Abstract

(Chemical Equation Presented) The reaction of dimedone with 1-(2-alkenoyl)-4-bromo-3,5-dimethylpyrazoles in THF, catalyzed by catalytic amounts of both DBFOX/Ph-nickel-(II) perchlorate trihydrate and 2,2,6,6-tetramethylpiperidine, in the presence of acetic anhydride in THF produces the corresponding enol lactones in high enantioselectivities through enantioselective Michael additions followed by cyclization with removal of the pyrazole auxiliary. Other related nucleophile precursors can be successfully applied in the enantioselective enol lactone synthesis under the double catalytic conditions.

Original languageEnglish
Pages (from-to)979-981
Number of pages3
JournalOrganic Letters
Volume7
Issue number6
DOIs
Publication statusPublished - Mar 17 2005

Fingerprint

nucleophiles
Lactones
anhydrides
perchlorates
nickel
Nucleophiles
Enantioselectivity
Cyclization
synthesis
Nickel
perchlorate
pyrazole
dimedone
acetic anhydride
2,2,6,6-tetramethylpiperidide
3,5-dimethylpyrazole

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Enantioselective enol lactone synthesis under double catalytic conditions. / Itoh, Kennosuke; Hasegawa, Masayuki; Tanaka, Junji; Kanemasa, Shuji.

In: Organic Letters, Vol. 7, No. 6, 17.03.2005, p. 979-981.

Research output: Contribution to journalArticle

Itoh, Kennosuke ; Hasegawa, Masayuki ; Tanaka, Junji ; Kanemasa, Shuji. / Enantioselective enol lactone synthesis under double catalytic conditions. In: Organic Letters. 2005 ; Vol. 7, No. 6. pp. 979-981.
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