An NMR method for assigning relative stereochemistry to β-hydroxy ketones deriving from aldol reactions of methyl ketones

William R. Roush; Thomas D. Bannister; Michael D. Wendt; Michael S. VanNieuwenhze; Darin J. Gustin; Garrett J. Dilley; Gregory C. Lane; Karl A. Scheidt; William J. Smith

doi:10.1021/jo0164148

An NMR method for assigning relative stereochemistry to β-hydroxy ketones deriving from aldol reactions of methyl ketones

William R. Roush^*, Thomas D. Bannister, Michael D. Wendt, Michael S. VanNieuwenhze, Darin J. Gustin, Garrett J. Dilley, Gregory C. Lane, Karl A. Scheidt, William J. Smith

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

35 Scopus citations

Abstract

We describe a simple ¹H NMR analysis that permits the stereochemistry of β-hydroxy ketones to be assigned by visual inspection of the ABX patterns for the α-methylene unit of the β-hydroxy ketone in the ¹H NMR spectra. This method has been verified by application to a wide range of β-hydroxy ketones deriving from aldol reactions of chiral aldehydes with a variety of chiral and achiral methyl ketone enolates (see Tables 1 and 2). The stereochemistry of 54 of these compounds have been assigned by rigorous chemical methods.

Original language	English (US)
Pages (from-to)	4284-4289
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	67
Issue number	12
DOIs	https://doi.org/10.1021/jo0164148
State	Published - Jun 14 2002

ASJC Scopus subject areas

Organic Chemistry

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title = "An NMR method for assigning relative stereochemistry to β-hydroxy ketones deriving from aldol reactions of methyl ketones",

abstract = "We describe a simple 1H NMR analysis that permits the stereochemistry of β-hydroxy ketones to be assigned by visual inspection of the ABX patterns for the α-methylene unit of the β-hydroxy ketone in the 1H NMR spectra. This method has been verified by application to a wide range of β-hydroxy ketones deriving from aldol reactions of chiral aldehydes with a variety of chiral and achiral methyl ketone enolates (see Tables 1 and 2). The stereochemistry of 54 of these compounds have been assigned by rigorous chemical methods.",

author = "Roush, {William R.} and Bannister, {Thomas D.} and Wendt, {Michael D.} and VanNieuwenhze, {Michael S.} and Gustin, {Darin J.} and Dilley, {Garrett J.} and Lane, {Gregory C.} and Scheidt, {Karl A.} and Smith, {William J.}",

year = "2002",

month = jun,

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doi = "10.1021/jo0164148",

language = "English (US)",

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journal = "Journal of Organic Chemistry",

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T1 - An NMR method for assigning relative stereochemistry to β-hydroxy ketones deriving from aldol reactions of methyl ketones

AU - Roush, William R.

AU - Bannister, Thomas D.

AU - Wendt, Michael D.

AU - VanNieuwenhze, Michael S.

AU - Gustin, Darin J.

AU - Dilley, Garrett J.

AU - Lane, Gregory C.

AU - Scheidt, Karl A.

AU - Smith, William J.

PY - 2002/6/14

Y1 - 2002/6/14

N2 - We describe a simple 1H NMR analysis that permits the stereochemistry of β-hydroxy ketones to be assigned by visual inspection of the ABX patterns for the α-methylene unit of the β-hydroxy ketone in the 1H NMR spectra. This method has been verified by application to a wide range of β-hydroxy ketones deriving from aldol reactions of chiral aldehydes with a variety of chiral and achiral methyl ketone enolates (see Tables 1 and 2). The stereochemistry of 54 of these compounds have been assigned by rigorous chemical methods.

AB - We describe a simple 1H NMR analysis that permits the stereochemistry of β-hydroxy ketones to be assigned by visual inspection of the ABX patterns for the α-methylene unit of the β-hydroxy ketone in the 1H NMR spectra. This method has been verified by application to a wide range of β-hydroxy ketones deriving from aldol reactions of chiral aldehydes with a variety of chiral and achiral methyl ketone enolates (see Tables 1 and 2). The stereochemistry of 54 of these compounds have been assigned by rigorous chemical methods.

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U2 - 10.1021/jo0164148

DO - 10.1021/jo0164148

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AN - SCOPUS:0037077057

SN - 0022-3263

VL - 67

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 12

ER -

An NMR method for assigning relative stereochemistry to β-hydroxy ketones deriving from aldol reactions of methyl ketones

Abstract

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