Unprecedented migration of N-alkoxycarbonyl groups in protected pyroglutaminol

Lennart Bunch; Per-Ola Norrby; Karla Frydenvang; Povl Krogsgaard-Larsen; Ulf Madsen

Unprecedented migration of N-alkoxycarbonyl groups in protected pyroglutaminol

Lennart Bunch, Per-Ola Norrby, Karla Frydenvang, Povl Krogsgaard-Larsen, Ulf Madsen

Department of Chemistry

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

Cleavage of an O-silyl ether in an NBOC 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 KCbz and N-methoxycarbonyl groups.

Original language	English
Journal	Organic Letters
Volume	3
Issue number	3
Pages (from-to)	433-435
ISSN	1523-7060
Publication status	Published - 2001

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

abstract = "Cleavage of an O-silyl ether in an NBOC 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 KCbz and N-methoxycarbonyl groups.",

author = "Lennart Bunch and Per-Ola Norrby and Karla Frydenvang and Povl Krogsgaard-Larsen and Ulf Madsen",

year = "2001",

language = "English",

volume = "3",

pages = "433--435",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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TY - JOUR

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

AU - Bunch, Lennart

AU - Norrby, Per-Ola

AU - Frydenvang, Karla

AU - Krogsgaard-Larsen, Povl

AU - Madsen, Ulf

PY - 2001

Y1 - 2001

N2 - Cleavage of an O-silyl ether in an NBOC 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 KCbz and N-methoxycarbonyl groups.

AB - Cleavage of an O-silyl ether in an NBOC 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 KCbz and N-methoxycarbonyl groups.

M3 - Journal article

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

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