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 | |
| State | Published - Aug 6 2010 |
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ASJC Scopus subject areas
- Organic Chemistry
- Physical and Theoretical Chemistry
- Biochemistry
- Medicine(all)
Cite this
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 journal › Article
}
TY - JOUR
T1 - Synthesis of substituted chromanones
T2 - An organocatalytic aldol/oxa-michael reaction
AU - Butler, Jeffrey D.
AU - Conrad, Wayne E.
AU - Lodewyk, Michael W.
AU - Fettinger, James C.
AU - Tantillo, Dean J.
AU - Kurth, Mark J.
PY - 2010/8/6
Y1 - 2010/8/6
N2 - (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.
AB - (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.
UR - http://www.scopus.com/inward/record.url?scp=77955167693&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=77955167693&partnerID=8YFLogxK
U2 - 10.1021/ol101221c
DO - 10.1021/ol101221c
M3 - Article
C2 - 20617821
AN - SCOPUS:77955167693
VL - 12
SP - 3410
EP - 3413
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 15
ER -