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

doi:10.1021/ol101221c

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

Chemistry

Research output: Contribution to journal › Article

16 Scopus citations

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 language	English (US)
Pages (from-to)	3410-3413
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	15
DOIs	https://doi.org/10.1021/ol101221c
State	Published - Aug 6 2010

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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

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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.",

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AU - Tantillo, Dean J.

AU - Kurth, Mark J.

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10.1021/ol101221c