Intramolecular Staudinger ligation: A powerful ring-closure method to form medium-sized lactams

Olivier David; Wim J.N. Meester; Hans Bieräugel; Hans E. Schoemaker; Henk Hiemstra; Jan H. Van Maarseveen

doi:10.1002/anie.200351930

Intramolecular Staudinger ligation: A powerful ring-closure method to form medium-sized lactams

Olivier David, Wim J.N. Meester, Hans Bieräugel, Hans E. Schoemaker, Henk Hiemstra, Jan H. Van Maarseveen

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

96 Scopus citations

Abstract

Efficient access to medium-sized lactams from co-amino acids that are resistant to ring-closure by traditional strategies is enabled by an intramolecular Staudinger ligation approach. An undesired premature Staudinger reaction is avoided by protecting the phosphane-containing auxiliary as a borane complex (see scheme; dabco = 1,4-diazabicyclo[2.2.2]octane).

Original language	English
Pages (from-to)	4373-4375
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	42
Issue number	36
DOIs	https://doi.org/10.1002/anie.200351930
State	Published - Sep 22 2003
Externally published	Yes

Keywords

Cyclization
Lactams
Medium-ring compounds
Ring contraction
Synthetic methods

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10.1002/anie.200351930

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abstract = "Efficient access to medium-sized lactams from co-amino acids that are resistant to ring-closure by traditional strategies is enabled by an intramolecular Staudinger ligation approach. An undesired premature Staudinger reaction is avoided by protecting the phosphane-containing auxiliary as a borane complex (see scheme; dabco = 1,4-diazabicyclo[2.2.2]octane).",

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author = "Olivier David and Meester, {Wim J.N.} and Hans Bier{\"a}ugel and Schoemaker, {Hans E.} and Henk Hiemstra and {Van Maarseveen}, {Jan H.}",

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T2 - A powerful ring-closure method to form medium-sized lactams

AU - David, Olivier

AU - Meester, Wim J.N.

AU - Bieräugel, Hans

AU - Schoemaker, Hans E.

AU - Hiemstra, Henk

AU - Van Maarseveen, Jan H.

PY - 2003/9/22

Y1 - 2003/9/22

N2 - Efficient access to medium-sized lactams from co-amino acids that are resistant to ring-closure by traditional strategies is enabled by an intramolecular Staudinger ligation approach. An undesired premature Staudinger reaction is avoided by protecting the phosphane-containing auxiliary as a borane complex (see scheme; dabco = 1,4-diazabicyclo[2.2.2]octane).

AB - Efficient access to medium-sized lactams from co-amino acids that are resistant to ring-closure by traditional strategies is enabled by an intramolecular Staudinger ligation approach. An undesired premature Staudinger reaction is avoided by protecting the phosphane-containing auxiliary as a borane complex (see scheme; dabco = 1,4-diazabicyclo[2.2.2]octane).

KW - Cyclization

KW - Lactams

KW - Medium-ring compounds

KW - Ring contraction

KW - Synthetic methods

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U2 - 10.1002/anie.200351930

DO - 10.1002/anie.200351930

M3 - Artículo

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 36

ER -

Intramolecular Staudinger ligation: A powerful ring-closure method to form medium-sized lactams

Abstract

Keywords

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