The synthesis of functionalised beta- and gamma-lactams by cyclisation of enamides using copper(I) or ruthenium(II)

J S  Bryans; N E A  Chessum; A F  Parsons; F  Ghelfi

The synthesis of functionalised beta- and gamma-lactams by cyclisation of enamides using copper(I) or ruthenium(II)

J S Bryans, N E A Chessum, A F Parsons, F Ghelfi

Chemistry

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

Abstract

Cyclisation of a variety of halo-enamides with copper(I) or ruthenium(II) complexes has been investigated. The regioselectivity of the radical cyclisation, which can proceed via either a 4-exo or 5-endo pathway, to form beta- or gamma -lactam products respectively, is determined by the nature of the metal oxidant and the reaction conditions. Thus, whereas copper(I)bipyridine reactions give predominantly gamma -lactams, the use of copper(I)/TMEDA or dichlorotris(triphenylphosphine)ruthenium(II) affords mainly beta -lactams. (C) 2001 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	2901-2905
Number of pages	5
Journal	Tetrahedron Letters
Volume	42
Issue number	15
Publication status	Published - 9 Apr 2001

Keywords

copper and compounds
lactams
radicals and radical reactions
ruthenium and compounds
MEDIATED RADICAL CYCLIZATION
ALPHA-HALO AMIDES
SUBSTITUTED PYRROLIDINONES
SECONDARY AMIDES
5-ENDO-TRIG
TEMPERATURE
4-EXO-TRIG
ATOM

Cite this

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title = "The synthesis of functionalised beta- and gamma-lactams by cyclisation of enamides using copper(I) or ruthenium(II)",

abstract = "Cyclisation of a variety of halo-enamides with copper(I) or ruthenium(II) complexes has been investigated. The regioselectivity of the radical cyclisation, which can proceed via either a 4-exo or 5-endo pathway, to form beta- or gamma -lactam products respectively, is determined by the nature of the metal oxidant and the reaction conditions. Thus, whereas copper(I)bipyridine reactions give predominantly gamma -lactams, the use of copper(I)/TMEDA or dichlorotris(triphenylphosphine)ruthenium(II) affords mainly beta -lactams. (C) 2001 Elsevier Science Ltd. All rights reserved.",

keywords = "copper and compounds, lactams, radicals and radical reactions, ruthenium and compounds, MEDIATED RADICAL CYCLIZATION, ALPHA-HALO AMIDES, SUBSTITUTED PYRROLIDINONES, SECONDARY AMIDES, 5-ENDO-TRIG, TEMPERATURE, 4-EXO-TRIG, ATOM",

author = "Bryans, {J S} and Chessum, {N E A} and Parsons, {A F} and F Ghelfi",

year = "2001",

month = apr,

day = "9",

language = "English",

volume = "42",

pages = "2901--2905",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "15",

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TY - JOUR

T1 - The synthesis of functionalised beta- and gamma-lactams by cyclisation of enamides using copper(I) or ruthenium(II)

AU - Bryans, J S

AU - Chessum, N E A

AU - Parsons, A F

AU - Ghelfi, F

PY - 2001/4/9

Y1 - 2001/4/9

N2 - Cyclisation of a variety of halo-enamides with copper(I) or ruthenium(II) complexes has been investigated. The regioselectivity of the radical cyclisation, which can proceed via either a 4-exo or 5-endo pathway, to form beta- or gamma -lactam products respectively, is determined by the nature of the metal oxidant and the reaction conditions. Thus, whereas copper(I)bipyridine reactions give predominantly gamma -lactams, the use of copper(I)/TMEDA or dichlorotris(triphenylphosphine)ruthenium(II) affords mainly beta -lactams. (C) 2001 Elsevier Science Ltd. All rights reserved.

AB - Cyclisation of a variety of halo-enamides with copper(I) or ruthenium(II) complexes has been investigated. The regioselectivity of the radical cyclisation, which can proceed via either a 4-exo or 5-endo pathway, to form beta- or gamma -lactam products respectively, is determined by the nature of the metal oxidant and the reaction conditions. Thus, whereas copper(I)bipyridine reactions give predominantly gamma -lactams, the use of copper(I)/TMEDA or dichlorotris(triphenylphosphine)ruthenium(II) affords mainly beta -lactams. (C) 2001 Elsevier Science Ltd. All rights reserved.

KW - copper and compounds

KW - lactams

KW - radicals and radical reactions

KW - ruthenium and compounds

KW - MEDIATED RADICAL CYCLIZATION

KW - ALPHA-HALO AMIDES

KW - SUBSTITUTED PYRROLIDINONES

KW - SECONDARY AMIDES

KW - 5-ENDO-TRIG

KW - TEMPERATURE

KW - 4-EXO-TRIG

KW - ATOM

M3 - Article

SN - 0040-4039

VL - 42

SP - 2901

EP - 2905

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 15

ER -