Generation and hydrolysis of N-acyloxazolinium salts allowing regiospecific acylation of chiral amino alcohols

R Alan Aitken; Alexandra Martha Zoya Slawin; Andrew Wilson

doi:10.1007/s10593-020-02707-3

Generation and hydrolysis of N-acyloxazolinium salts allowing regiospecific acylation of chiral amino alcohols

R Alan Aitken, Alexandra Martha Zoya Slawin, Andrew Wilson

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Abstract

In an attempt to form 2-alkylidene-1,3-oxazolidines, chiral 2-oxazolines have been N-alkylated and N-acylated. Two new N-methyloxazolinium salts have been prepared and characterised but base treatment resulted in their decomposition. In contrast, attempts to isolate three N-benzoyloxazolinium salts gave the products of their ring hydrolysis: unsymmetrically diacylated amino alcohols whose structure was confirmed by x-ray diffraction in one case. Overall the method allows stepwise regiospecific N,O-diacylation of 1,2-amino alcohols.

Original language	English
Pages (from-to)	611-614
Number of pages	4
Journal	Chemistry of Heterocyclic Compounds
Volume	56
Issue number	5
Early online date	2 Jun 2020
DOIs	https://doi.org/10.1007/s10593-020-02707-3
Publication status	Published - 15 Jun 2020

Keywords

Amino alcohols
Acylation
Oxazolines
Oxazolinium salts
Hydrolysis

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10.1007/s10593-020-02707-3

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Copyright © 2020 Springer Science+Business Media, LLC. This work has been made available online in accordance with publisher policies or with permission. Permission for further reuse of this content should be sought from the publisher or the rights holder. This is the author created accepted manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1007/s10593-020-02707-3
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Generation and hydrolysis of N-acyloxazolinium salts allowing regiospecific acylation of chiral amino alcohols (dataset)
Aitken, R. A. (Creator) & Slawin, A. M. Z. (Creator), Cambridge Crystallographic Data Centre, 18 Sept 2020
https://dx.doi.org/10.5517/ccdc.csd.cc20gsw5
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title = "Generation and hydrolysis of N-acyloxazolinium salts allowing regiospecific acylation of chiral amino alcohols",

abstract = "In an attempt to form 2-alkylidene-1,3-oxazolidines, chiral 2-oxazolines have been N-alkylated and N-acylated. Two new N-methyloxazolinium salts have been prepared and characterised but base treatment resulted in their decomposition. In contrast, attempts to isolate three N-benzoyloxazolinium salts gave the products of their ring hydrolysis: unsymmetrically diacylated amino alcohols whose structure was confirmed by x-ray diffraction in one case. Overall the method allows stepwise regiospecific N,O-diacylation of 1,2-amino alcohols.",

keywords = "Amino alcohols, Acylation, Oxazolines, Oxazolinium salts, Hydrolysis",

author = "Aitken, {R Alan} and Slawin, {Alexandra Martha Zoya} and Andrew Wilson",

year = "2020",

month = jun,

day = "15",

doi = "10.1007/s10593-020-02707-3",

language = "English",

volume = "56",

pages = "611--614",

journal = "Chemistry of Heterocyclic Compounds",

issn = "1573-8353",

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number = "5",

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TY - JOUR

T1 - Generation and hydrolysis of N-acyloxazolinium salts allowing regiospecific acylation of chiral amino alcohols

AU - Aitken, R Alan

AU - Slawin, Alexandra Martha Zoya

AU - Wilson, Andrew

PY - 2020/6/15

Y1 - 2020/6/15

N2 - In an attempt to form 2-alkylidene-1,3-oxazolidines, chiral 2-oxazolines have been N-alkylated and N-acylated. Two new N-methyloxazolinium salts have been prepared and characterised but base treatment resulted in their decomposition. In contrast, attempts to isolate three N-benzoyloxazolinium salts gave the products of their ring hydrolysis: unsymmetrically diacylated amino alcohols whose structure was confirmed by x-ray diffraction in one case. Overall the method allows stepwise regiospecific N,O-diacylation of 1,2-amino alcohols.

AB - In an attempt to form 2-alkylidene-1,3-oxazolidines, chiral 2-oxazolines have been N-alkylated and N-acylated. Two new N-methyloxazolinium salts have been prepared and characterised but base treatment resulted in their decomposition. In contrast, attempts to isolate three N-benzoyloxazolinium salts gave the products of their ring hydrolysis: unsymmetrically diacylated amino alcohols whose structure was confirmed by x-ray diffraction in one case. Overall the method allows stepwise regiospecific N,O-diacylation of 1,2-amino alcohols.

KW - Amino alcohols

KW - Acylation

KW - Oxazolines

KW - Oxazolinium salts

KW - Hydrolysis

U2 - 10.1007/s10593-020-02707-3

DO - 10.1007/s10593-020-02707-3

M3 - Article

SN - 1573-8353

VL - 56

SP - 611

EP - 614

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

IS - 5

ER -

Generation and hydrolysis of N-acyloxazolinium salts allowing regiospecific acylation of chiral amino alcohols

Abstract

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Generation and hydrolysis of N-acyloxazolinium salts allowing regiospecific acylation of chiral amino alcohols (dataset)

Cite this