Chiral relay in NHC-mediated asymmetric beta-lactam synthesis II; asymmetry from NHCs derived from acyclic 1,2-diamines

Nicolas Duguet; Adele Donaldson; Stuart M. Leckie; Eddy A. Kallstrom; Craig D. Campbell; Peter Shapland; Thomas B. Brown; Alexandra M. Z. Slawin; Andrew D. Smith

doi:10.1016/j.tetasy.2010.03.002

Chiral relay in NHC-mediated asymmetric beta-lactam synthesis II; asymmetry from NHCs derived from acyclic 1,2-diamines

Nicolas Duguet, Adele Donaldson, Stuart M. Leckie, Eddy A. Kallstrom, Craig D. Campbell, Peter Shapland, Thomas B. Brown, Alexandra M. Z. Slawin, Andrew D. Smith

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

Abstract

The synthesis of a range of imidazolinium salts derived from acyclic 1,2-diamines, and an evaluation of the reactivity and asymmetric induction of the corresponding NHCs as catalysts for the asymmetric synthesis of beta-lactams, is reported. An N-methyl-substituted NHC derived from (1R,2R)-1,2-diphenylethanediamine shows optimal reactivity and enantioselectivity in this series, in contrast to that observed with NHCs derived from (1R,2R)-cyclohexane-1,2-diamine. (C) 2010 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	601-616
Number of pages	16
Journal	Tetrahedron: Asymmetry
Volume	21
Issue number	5
DOIs	https://doi.org/10.1016/j.tetasy.2010.03.002
Publication status	Published - 30 Mar 2010

Keywords

N-HETEROCYCLIC CARBENE
ALPHA-AMINO-ACIDS
HIGHLY ENANTIOSELECTIVE SYNTHESIS
CATALYZED CONJUGATE ADDITION
C-CARBOXYL TRANSFER
LEWIS-ACID
DISUBSTITUTED KETENES
4+2 CYCLOADDITION
CONVEY ASYMMETRY
ACHIRAL LIGANDS

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10.1016/j.tetasy.2010.03.002

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@article{492314af0aef4c8eaaf5994ad45a0f87,

title = "Chiral relay in NHC-mediated asymmetric beta-lactam synthesis II; asymmetry from NHCs derived from acyclic 1,2-diamines",

abstract = "The synthesis of a range of imidazolinium salts derived from acyclic 1,2-diamines, and an evaluation of the reactivity and asymmetric induction of the corresponding NHCs as catalysts for the asymmetric synthesis of beta-lactams, is reported. An N-methyl-substituted NHC derived from (1R,2R)-1,2-diphenylethanediamine shows optimal reactivity and enantioselectivity in this series, in contrast to that observed with NHCs derived from (1R,2R)-cyclohexane-1,2-diamine. (C) 2010 Elsevier Ltd. All rights reserved.",

keywords = "N-HETEROCYCLIC CARBENE, ALPHA-AMINO-ACIDS, HIGHLY ENANTIOSELECTIVE SYNTHESIS, CATALYZED CONJUGATE ADDITION, C-CARBOXYL TRANSFER, LEWIS-ACID, DISUBSTITUTED KETENES, 4+2 CYCLOADDITION, CONVEY ASYMMETRY, ACHIRAL LIGANDS",

author = "Nicolas Duguet and Adele Donaldson and Leckie, \{Stuart M.\} and Kallstrom, \{Eddy A.\} and Campbell, \{Craig D.\} and Peter Shapland and Brown, \{Thomas B.\} and Slawin, \{Alexandra M. Z.\} and Smith, \{Andrew D.\}",

year = "2010",

month = mar,

day = "30",

doi = "10.1016/j.tetasy.2010.03.002",

language = "English",

volume = "21",

pages = "601--616",

journal = "Tetrahedron: Asymmetry",

issn = "0957-4166",

publisher = "Elsevier",

number = "5",

}

TY - JOUR

T1 - Chiral relay in NHC-mediated asymmetric beta-lactam synthesis II; asymmetry from NHCs derived from acyclic 1,2-diamines

AU - Duguet, Nicolas

AU - Donaldson, Adele

AU - Leckie, Stuart M.

AU - Kallstrom, Eddy A.

AU - Campbell, Craig D.

AU - Shapland, Peter

AU - Brown, Thomas B.

AU - Slawin, Alexandra M. Z.

AU - Smith, Andrew D.

PY - 2010/3/30

Y1 - 2010/3/30

N2 - The synthesis of a range of imidazolinium salts derived from acyclic 1,2-diamines, and an evaluation of the reactivity and asymmetric induction of the corresponding NHCs as catalysts for the asymmetric synthesis of beta-lactams, is reported. An N-methyl-substituted NHC derived from (1R,2R)-1,2-diphenylethanediamine shows optimal reactivity and enantioselectivity in this series, in contrast to that observed with NHCs derived from (1R,2R)-cyclohexane-1,2-diamine. (C) 2010 Elsevier Ltd. All rights reserved.

AB - The synthesis of a range of imidazolinium salts derived from acyclic 1,2-diamines, and an evaluation of the reactivity and asymmetric induction of the corresponding NHCs as catalysts for the asymmetric synthesis of beta-lactams, is reported. An N-methyl-substituted NHC derived from (1R,2R)-1,2-diphenylethanediamine shows optimal reactivity and enantioselectivity in this series, in contrast to that observed with NHCs derived from (1R,2R)-cyclohexane-1,2-diamine. (C) 2010 Elsevier Ltd. All rights reserved.

KW - N-HETEROCYCLIC CARBENE

KW - ALPHA-AMINO-ACIDS

KW - HIGHLY ENANTIOSELECTIVE SYNTHESIS

KW - CATALYZED CONJUGATE ADDITION

KW - C-CARBOXYL TRANSFER

KW - LEWIS-ACID

KW - DISUBSTITUTED KETENES

KW - 4+2 CYCLOADDITION

KW - CONVEY ASYMMETRY

KW - ACHIRAL LIGANDS

UR - https://www.scopus.com/pages/publications/77953132255

U2 - 10.1016/j.tetasy.2010.03.002

DO - 10.1016/j.tetasy.2010.03.002

M3 - Article

SN - 0957-4166

VL - 21

SP - 601

EP - 616

JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

IS - 5

ER -

Chiral relay in NHC-mediated asymmetric beta-lactam synthesis II; asymmetry from NHCs derived from acyclic 1,2-diamines

Abstract

Keywords

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