Unprecedented migration of N-alkoxycarbonyl groups in protected pyroglutaminol

L Bunch; Per-Ola Norrby; Karla Andrea Frydenvang; P Krogsgaard-Larsen; U Madsen

Unprecedented migration of N-alkoxycarbonyl groups in protected pyroglutaminol

L Bunch, Per-Ola Norrby, Karla Andrea Frydenvang, P Krogsgaard-Larsen, U Madsen

21 Citations (Scopus)

Abstract

[figure: see text] Cleavage of an O-silyl ether in an N-BOC-protected pyroglutaminol using TBAF led to an unprecedented migration of the BOC group. An investigation of the mechanism, based on experimental data and quantum mechanical calculations, is presented. Similar migration was observed for N-Cbz and N-methoxycarbonyl groups.

Original language	English
Journal	Organic Letters
Volume	3
Issue number	3
Pages (from-to)	433-5
Number of pages	3
ISSN	1523-7060
Publication status	Published - 2001

Keywords

Formic Acid Esters
Glutamic Acid
Magnetic Resonance Spectroscopy
Molecular Structure
Pyrroles
Quantum Theory
X-Ray Diffraction

Cite this

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title = "Unprecedented migration of N-alkoxycarbonyl groups in protected pyroglutaminol",

abstract = "[figure: see text] Cleavage of an O-silyl ether in an N-BOC-protected pyroglutaminol using TBAF led to an unprecedented migration of the BOC group. An investigation of the mechanism, based on experimental data and quantum mechanical calculations, is presented. Similar migration was observed for N-Cbz and N-methoxycarbonyl groups.",

keywords = "Formic Acid Esters, Glutamic Acid, Magnetic Resonance Spectroscopy, Molecular Structure, Pyrroles, Quantum Theory, X-Ray Diffraction",

author = "L Bunch and Per-Ola Norrby and Frydenvang, {Karla Andrea} and P Krogsgaard-Larsen and U Madsen",

year = "2001",

language = "English",

volume = "3",

pages = "433--5",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "3",

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TY - JOUR

T1 - Unprecedented migration of N-alkoxycarbonyl groups in protected pyroglutaminol

AU - Bunch, L

AU - Norrby, Per-Ola

AU - Frydenvang, Karla Andrea

AU - Krogsgaard-Larsen, P

AU - Madsen, U

PY - 2001

Y1 - 2001

N2 - [figure: see text] Cleavage of an O-silyl ether in an N-BOC-protected pyroglutaminol using TBAF led to an unprecedented migration of the BOC group. An investigation of the mechanism, based on experimental data and quantum mechanical calculations, is presented. Similar migration was observed for N-Cbz and N-methoxycarbonyl groups.

AB - [figure: see text] Cleavage of an O-silyl ether in an N-BOC-protected pyroglutaminol using TBAF led to an unprecedented migration of the BOC group. An investigation of the mechanism, based on experimental data and quantum mechanical calculations, is presented. Similar migration was observed for N-Cbz and N-methoxycarbonyl groups.

KW - Formic Acid Esters

KW - Glutamic Acid

KW - Magnetic Resonance Spectroscopy

KW - Molecular Structure

KW - Pyrroles

KW - Quantum Theory

KW - X-Ray Diffraction

M3 - Journal article

C2 - 11428032

SN - 1523-7060

VL - 3

SP - 433

EP - 435

JO - Organic Letters

JF - Organic Letters

IS - 3

ER -

Unprecedented migration of N-alkoxycarbonyl groups in protected pyroglutaminol

Abstract

Keywords

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