Direct conversion of esters to hydroxyamides on solid support - A key step en route to bisoxazoline ligands

Avi Weissberg; Moshe Portnoy

doi:10.1055/s-2002-19746

Direct conversion of esters to hydroxyamides on solid support - A key step en route to bisoxazoline ligands

Avi Weissberg, Moshe Portnoy^*

^*Corresponding author for this work

School of Chemistry

Tel Aviv University

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

4 Scopus citations

Abstract

A method for converting esters into β-hydroxyamides via their direct reaction with β-aminoalcohols was implemented for the first time on solid support. The transformation is performed under basic conditions and presumably includes transesterification followed by rapid intramolecular O,N-acyl transfer. The technique was successfully tested on monoesters as well as malonates. The transformation of malonates is a key step in the on-resin assembly of bisoxazoline ligands, demonstrated here for the first time.

Original language	English
Pages (from-to)	247-250
Number of pages	4
Journal	Synlett
Issue number	2
DOIs	https://doi.org/10.1055/s-2002-19746
State	Published - 2002

Keywords

Amides
Aminoalcohols
Aminolysis
Oxazolines
Solid-phase synthesis

Access to Document

10.1055/s-2002-19746

Cite this

@article{85b61de8c60a4e488023a9b7f5979df9,

title = "Direct conversion of esters to hydroxyamides on solid support - A key step en route to bisoxazoline ligands",

abstract = "A method for converting esters into β-hydroxyamides via their direct reaction with β-aminoalcohols was implemented for the first time on solid support. The transformation is performed under basic conditions and presumably includes transesterification followed by rapid intramolecular O,N-acyl transfer. The technique was successfully tested on monoesters as well as malonates. The transformation of malonates is a key step in the on-resin assembly of bisoxazoline ligands, demonstrated here for the first time.",

keywords = "Amides, Aminoalcohols, Aminolysis, Oxazolines, Solid-phase synthesis",

author = "Avi Weissberg and Moshe Portnoy",

year = "2002",

doi = "10.1055/s-2002-19746",

language = "אנגלית",

pages = "247--250",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "2",

}

TY - JOUR

T1 - Direct conversion of esters to hydroxyamides on solid support - A key step en route to bisoxazoline ligands

AU - Weissberg, Avi

AU - Portnoy, Moshe

PY - 2002

Y1 - 2002

N2 - A method for converting esters into β-hydroxyamides via their direct reaction with β-aminoalcohols was implemented for the first time on solid support. The transformation is performed under basic conditions and presumably includes transesterification followed by rapid intramolecular O,N-acyl transfer. The technique was successfully tested on monoesters as well as malonates. The transformation of malonates is a key step in the on-resin assembly of bisoxazoline ligands, demonstrated here for the first time.

AB - A method for converting esters into β-hydroxyamides via their direct reaction with β-aminoalcohols was implemented for the first time on solid support. The transformation is performed under basic conditions and presumably includes transesterification followed by rapid intramolecular O,N-acyl transfer. The technique was successfully tested on monoesters as well as malonates. The transformation of malonates is a key step in the on-resin assembly of bisoxazoline ligands, demonstrated here for the first time.

KW - Amides

KW - Aminoalcohols

KW - Aminolysis

KW - Oxazolines

KW - Solid-phase synthesis

UR - http://www.scopus.com/inward/record.url?scp=0036166977&partnerID=8YFLogxK

U2 - 10.1055/s-2002-19746

DO - 10.1055/s-2002-19746

M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???

AN - SCOPUS:0036166977

SN - 0936-5214

SP - 247

EP - 250

JO - Synlett

JF - Synlett

IS - 2

ER -

Direct conversion of esters to hydroxyamides on solid support - A key step en route to bisoxazoline ligands

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this