Synthesis of substituted chromanones: An organocatalytic aldol/oxa-michael reaction

Jeffrey D. Butler, Wayne E. Conrad, Michael W. Lodewyk, James C. Fettinger, Dean J. Tantillo, Mark J. Kurth

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

(Equation Presented). A diastereoselective organocatalytic aldol/oxa-Michael reaction has been developed to efficiently deliver medicinally relevant 2,3-ring-substituted chromanones. Development of this synthetic strategy revealed an unexpected kinetic anti-Saytzeff elimination; an origin for the observed selectivity is suggested on the basis of the results of quantum chemical calculations. This unusual kinetic selectivity necessitated an isomerization protocol that in turn led to the discovery of an intriguing Pd-mediated isomerization/intramolecular Friedel-Crafts-type alkylation.

Original languageEnglish (US)
Pages (from-to)3410-3413
Number of pages4
JournalOrganic Letters
Volume12
Issue number15
DOIs
StatePublished - Aug 6 2010

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Michael reaction
Isomerization
isomerization
selectivity
Kinetics
alkylation
Alkylation
kinetics
synthesis
elimination
vehicles
rings
3-hydroxybutanal

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry
  • Medicine(all)

Cite this

Butler, J. D., Conrad, W. E., Lodewyk, M. W., Fettinger, J. C., Tantillo, D. J., & Kurth, M. J. (2010). Synthesis of substituted chromanones: An organocatalytic aldol/oxa-michael reaction. Organic Letters, 12(15), 3410-3413. https://doi.org/10.1021/ol101221c

Synthesis of substituted chromanones : An organocatalytic aldol/oxa-michael reaction. / Butler, Jeffrey D.; Conrad, Wayne E.; Lodewyk, Michael W.; Fettinger, James C.; Tantillo, Dean J.; Kurth, Mark J.

In: Organic Letters, Vol. 12, No. 15, 06.08.2010, p. 3410-3413.

Research output: Contribution to journalArticle

Butler, JD, Conrad, WE, Lodewyk, MW, Fettinger, JC, Tantillo, DJ & Kurth, MJ 2010, 'Synthesis of substituted chromanones: An organocatalytic aldol/oxa-michael reaction', Organic Letters, vol. 12, no. 15, pp. 3410-3413. https://doi.org/10.1021/ol101221c
Butler JD, Conrad WE, Lodewyk MW, Fettinger JC, Tantillo DJ, Kurth MJ. Synthesis of substituted chromanones: An organocatalytic aldol/oxa-michael reaction. Organic Letters. 2010 Aug 6;12(15):3410-3413. https://doi.org/10.1021/ol101221c
Butler, Jeffrey D. ; Conrad, Wayne E. ; Lodewyk, Michael W. ; Fettinger, James C. ; Tantillo, Dean J. ; Kurth, Mark J. / Synthesis of substituted chromanones : An organocatalytic aldol/oxa-michael reaction. In: Organic Letters. 2010 ; Vol. 12, No. 15. pp. 3410-3413.
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