Enantioselective synthesis of (2R,3R)- and (2S,3S)-2-[(3-chlorophenyl)-(2- methoxyphenoxy)methyl]morpholine

Wayne W. Harding; Matthis Hodge; Zhixia Wang; William L. Woolverton; Damon Parrish; Jeffrey R. Deschamps; Thomas E. Prisinzano

doi:10.1016/j.tetasy.2005.06.012

Enantioselective synthesis of (2R,3R)- and (2S,3S)-2-[(3-chlorophenyl)-(2- methoxyphenoxy)methyl]morpholine

Wayne W. Harding
, Matthis Hodge
, Zhixia Wang
, William L. Woolverton
, Damon Parrish
, Jeffrey R. Deschamps
, Thomas E. Prisinzano

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

15 Scopus citations

Abstract

The enantioselective synthesis of the (R,R)- and (S,S)-enantiomers of 1 from commercially available 3-chlorocinnamic acid is reported. The Sharpless asymmetric epoxidation was used to establish the stereocenters in the synthesis of both enantiomers of 1.

Original language	English
Pages (from-to)	2249-2256
Number of pages	8
Journal	Tetrahedron Asymmetry
Volume	16
Issue number	13
DOIs	https://doi.org/10.1016/j.tetasy.2005.06.012
State	Published - Jul 4 2005

Bibliographical note

Funding Information:
The authors (W.W.H., T.E.P.) thank the Biological Sciences Funding Program of the University of Iowa and (W.L.W.) the National Institute on Drug Abuse for financial support. W.L.W. is a recipient of National Institute on Drug Abuse grant K05-DA15343. The X-ray crystallographic work was supported in part by the National Institute on Drug Abuse, NIH, DHHS, and the Office of Naval Research. The authors also thank Vic Parcell and Lynn Teesch of the High Resolution Mass Spectrometry Facility, University of Iowa for mass spectral analysis.

Funding

The authors (W.W.H., T.E.P.) thank the Biological Sciences Funding Program of the University of Iowa and (W.L.W.) the National Institute on Drug Abuse for financial support. W.L.W. is a recipient of National Institute on Drug Abuse grant K05-DA15343. The X-ray crystallographic work was supported in part by the National Institute on Drug Abuse, NIH, DHHS, and the Office of Naval Research. The authors also thank Vic Parcell and Lynn Teesch of the High Resolution Mass Spectrometry Facility, University of Iowa for mass spectral analysis.

Funders
National Institutes of Health (NIH)
Office of Naval Research
National Institute on Drug Abuse
University of Northern Iowa
Department of Health and Human Services, State Government of Victoria

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1016/j.tetasy.2005.06.012

Cite this

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title = "Enantioselective synthesis of (2R,3R)- and (2S,3S)-2-[(3-chlorophenyl)-(2- methoxyphenoxy)methyl]morpholine",

abstract = "The enantioselective synthesis of the (R,R)- and (S,S)-enantiomers of 1 from commercially available 3-chlorocinnamic acid is reported. The Sharpless asymmetric epoxidation was used to establish the stereocenters in the synthesis of both enantiomers of 1.",

author = "Harding, \{Wayne W.\} and Matthis Hodge and Zhixia Wang and Woolverton, \{William L.\} and Damon Parrish and Deschamps, \{Jeffrey R.\} and Prisinzano, \{Thomas E.\}",

note = "Funding Information: The authors (W.W.H., T.E.P.) thank the Biological Sciences Funding Program of the University of Iowa and (W.L.W.) the National Institute on Drug Abuse for financial support. W.L.W. is a recipient of National Institute on Drug Abuse grant K05-DA15343. The X-ray crystallographic work was supported in part by the National Institute on Drug Abuse, NIH, DHHS, and the Office of Naval Research. The authors also thank Vic Parcell and Lynn Teesch of the High Resolution Mass Spectrometry Facility, University of Iowa for mass spectral analysis. ",

year = "2005",

month = jul,

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doi = "10.1016/j.tetasy.2005.06.012",

language = "English",

volume = "16",

pages = "2249--2256",

number = "13",

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TY - JOUR

T1 - Enantioselective synthesis of (2R,3R)- and (2S,3S)-2-[(3-chlorophenyl)-(2- methoxyphenoxy)methyl]morpholine

AU - Harding, Wayne W.

AU - Hodge, Matthis

AU - Wang, Zhixia

AU - Woolverton, William L.

AU - Parrish, Damon

AU - Deschamps, Jeffrey R.

AU - Prisinzano, Thomas E.

N1 - Funding Information: The authors (W.W.H., T.E.P.) thank the Biological Sciences Funding Program of the University of Iowa and (W.L.W.) the National Institute on Drug Abuse for financial support. W.L.W. is a recipient of National Institute on Drug Abuse grant K05-DA15343. The X-ray crystallographic work was supported in part by the National Institute on Drug Abuse, NIH, DHHS, and the Office of Naval Research. The authors also thank Vic Parcell and Lynn Teesch of the High Resolution Mass Spectrometry Facility, University of Iowa for mass spectral analysis.

PY - 2005/7/4

Y1 - 2005/7/4

N2 - The enantioselective synthesis of the (R,R)- and (S,S)-enantiomers of 1 from commercially available 3-chlorocinnamic acid is reported. The Sharpless asymmetric epoxidation was used to establish the stereocenters in the synthesis of both enantiomers of 1.

AB - The enantioselective synthesis of the (R,R)- and (S,S)-enantiomers of 1 from commercially available 3-chlorocinnamic acid is reported. The Sharpless asymmetric epoxidation was used to establish the stereocenters in the synthesis of both enantiomers of 1.

UR - https://www.scopus.com/pages/publications/22044439589

UR - https://www.scopus.com/pages/publications/22044439589#tab=citedBy

U2 - 10.1016/j.tetasy.2005.06.012

DO - 10.1016/j.tetasy.2005.06.012

M3 - Article

AN - SCOPUS:22044439589

SN - 0957-4166

VL - 16

SP - 2249

EP - 2256

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 13

ER -

Enantioselective synthesis of (2R,3R)- and (2S,3S)-2-[(3-chlorophenyl)-(2- methoxyphenoxy)methyl]morpholine

Abstract

Bibliographical note

Funding

ASJC Scopus subject areas

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