Determination of Configuration and Conformation of Isoxazolidines by Nuclear Overhauser Effect Difference Spectroscopy

Philip DeShong; C. Michael Dicken; Ronald R. Staib; Alan J. Freyer; Steven M. Weinreb

doi:10.1021/jo00144a002

Determination of Configuration and Conformation of Isoxazolidines by Nuclear Overhauser Effect Difference Spectroscopy

Philip DeShong, C. Michael Dicken, Ronald R. Staib, Alan J. Freyer, Steven M. Weinreb

Chemistry

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

100 Scopus citations

Abstract

The configurations of isoxazolidines 2, 3, 5, 7, and 10–12 have been assigned by analysis of NMR coupling constants and by nuclear Overhauser effect difference spectroscopy (NOEDS). The preferred solution conformations of isoxazolidines 3 and 5 were determined to be as in 3A/5A. It is proposed that these conformations are adopted to take advantage of the anomeric effect and to alleviate the unfavorable stereoelectronic lone pair-lone pair interaction in the N-O portion of the molecule (gauche effect).

Original language	English (US)
Pages (from-to)	4397-4403
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	47
Issue number	23
DOIs	https://doi.org/10.1021/jo00144a002
State	Published - 1982

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo00144a002

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title = "Determination of Configuration and Conformation of Isoxazolidines by Nuclear Overhauser Effect Difference Spectroscopy",

abstract = "The configurations of isoxazolidines 2, 3, 5, 7, and 10–12 have been assigned by analysis of NMR coupling constants and by nuclear Overhauser effect difference spectroscopy (NOEDS). The preferred solution conformations of isoxazolidines 3 and 5 were determined to be as in 3A/5A. It is proposed that these conformations are adopted to take advantage of the anomeric effect and to alleviate the unfavorable stereoelectronic lone pair-lone pair interaction in the N-O portion of the molecule (gauche effect).",

author = "Philip DeShong and Dicken, {C. Michael} and Staib, {Ronald R.} and Freyer, {Alan J.} and Weinreb, {Steven M.}",

year = "1982",

doi = "10.1021/jo00144a002",

language = "English (US)",

volume = "47",

pages = "4397--4403",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "23",

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TY - JOUR

T1 - Determination of Configuration and Conformation of Isoxazolidines by Nuclear Overhauser Effect Difference Spectroscopy

AU - DeShong, Philip

AU - Dicken, C. Michael

AU - Staib, Ronald R.

AU - Freyer, Alan J.

AU - Weinreb, Steven M.

PY - 1982

Y1 - 1982

N2 - The configurations of isoxazolidines 2, 3, 5, 7, and 10–12 have been assigned by analysis of NMR coupling constants and by nuclear Overhauser effect difference spectroscopy (NOEDS). The preferred solution conformations of isoxazolidines 3 and 5 were determined to be as in 3A/5A. It is proposed that these conformations are adopted to take advantage of the anomeric effect and to alleviate the unfavorable stereoelectronic lone pair-lone pair interaction in the N-O portion of the molecule (gauche effect).

AB - The configurations of isoxazolidines 2, 3, 5, 7, and 10–12 have been assigned by analysis of NMR coupling constants and by nuclear Overhauser effect difference spectroscopy (NOEDS). The preferred solution conformations of isoxazolidines 3 and 5 were determined to be as in 3A/5A. It is proposed that these conformations are adopted to take advantage of the anomeric effect and to alleviate the unfavorable stereoelectronic lone pair-lone pair interaction in the N-O portion of the molecule (gauche effect).

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U2 - 10.1021/jo00144a002

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 23

ER -

Determination of Configuration and Conformation of Isoxazolidines by Nuclear Overhauser Effect Difference Spectroscopy

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