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 › peer-review

21 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

ASJC Scopus subject areas

Organic Chemistry
Physical and Theoretical Chemistry
Biochemistry
Medicine(all)

Access to Document

10.1021/ol101221c

Cite this

@article{25b7f8e56b3c441e801e65b925458629,

title = "Synthesis of substituted chromanones: An organocatalytic aldol/oxa-michael reaction",

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.",

author = "Butler, {Jeffrey D.} and Conrad, {Wayne E.} and Lodewyk, {Michael W.} and Fettinger, {James C.} and Tantillo, {Dean J.} and Kurth, {Mark J.}",

year = "2010",

month = aug,

day = "6",

doi = "10.1021/ol101221c",

language = "English (US)",

volume = "12",

pages = "3410--3413",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "15",

}

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 -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this