Metal-mediated asymmetric alkylation using chiral N-heterocyclic carbenes derived from chiral amines

Richard E. Douthwaite

doi:10.1016/j.ccr.2006.08.003

Metal-mediated asymmetric alkylation using chiral N-heterocyclic carbenes derived from chiral amines

Richard E. Douthwaite

Chemistry

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

Abstract

The significant advances in achiral catalysis using N-heterocyclic carbene (NHC) metal complexes have prompted intense investigation of chiral NHC derivatives for use in asymmetric catalysis in recent years. Discovery of new chiral NHC catalysts is supported by the development of synthetic routes to chiral NHC ligands and their metal complexes. Here routes to chiral NHC ligands derived principally from chiral diamines will be outlined and metal complex structures described in the context of application to asymmetric catalysis. Emphasis will be placed on palladium and copper catalysed asymmetric alkylations that serve to illustrate the potential and some limitations of NHC-based asymmetric catalysts. (c) 2006 Elsevier B.V. All rights reserved.

Original language	English
Pages (from-to)	702-717
Number of pages	16
Journal	COORDINATION CHEMISTRY REVIEWS
Volume	251
Issue number	5-6
DOIs	https://doi.org/10.1016/j.ccr.2006.08.003
Publication status	Published - Mar 2007

Keywords

N-heterocyclic carbenes
catalysis
chirality
alkylation
palladium
copper
CATALYZED CONJUGATE ADDITION
ALLYLIC SUBSTITUTION-REACTION
ALKOXY-NHC LIGANDS
PALLADIUM(II) COMPLEXES
OLEFIN METATHESIS
RHODIUM COMPLEXES
GRIGNARD-REAGENTS
EFFICIENT
REACTIVITY
HYDROSILYLATION

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10.1016/j.ccr.2006.08.003

Cite this

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title = "Metal-mediated asymmetric alkylation using chiral N-heterocyclic carbenes derived from chiral amines",

abstract = "The significant advances in achiral catalysis using N-heterocyclic carbene (NHC) metal complexes have prompted intense investigation of chiral NHC derivatives for use in asymmetric catalysis in recent years. Discovery of new chiral NHC catalysts is supported by the development of synthetic routes to chiral NHC ligands and their metal complexes. Here routes to chiral NHC ligands derived principally from chiral diamines will be outlined and metal complex structures described in the context of application to asymmetric catalysis. Emphasis will be placed on palladium and copper catalysed asymmetric alkylations that serve to illustrate the potential and some limitations of NHC-based asymmetric catalysts. (c) 2006 Elsevier B.V. All rights reserved.",

keywords = "N-heterocyclic carbenes, catalysis, chirality, alkylation, palladium, copper, CATALYZED CONJUGATE ADDITION, ALLYLIC SUBSTITUTION-REACTION, ALKOXY-NHC LIGANDS, PALLADIUM(II) COMPLEXES, OLEFIN METATHESIS, RHODIUM COMPLEXES, GRIGNARD-REAGENTS, EFFICIENT, REACTIVITY, HYDROSILYLATION",

author = "Douthwaite, {Richard E.}",

year = "2007",

month = mar,

doi = "10.1016/j.ccr.2006.08.003",

language = "English",

volume = "251",

pages = "702--717",

journal = "COORDINATION CHEMISTRY REVIEWS",

issn = "0010-8545",

publisher = "Elsevier",

number = "5-6",

}

TY - JOUR

T1 - Metal-mediated asymmetric alkylation using chiral N-heterocyclic carbenes derived from chiral amines

AU - Douthwaite, Richard E.

PY - 2007/3

Y1 - 2007/3

N2 - The significant advances in achiral catalysis using N-heterocyclic carbene (NHC) metal complexes have prompted intense investigation of chiral NHC derivatives for use in asymmetric catalysis in recent years. Discovery of new chiral NHC catalysts is supported by the development of synthetic routes to chiral NHC ligands and their metal complexes. Here routes to chiral NHC ligands derived principally from chiral diamines will be outlined and metal complex structures described in the context of application to asymmetric catalysis. Emphasis will be placed on palladium and copper catalysed asymmetric alkylations that serve to illustrate the potential and some limitations of NHC-based asymmetric catalysts. (c) 2006 Elsevier B.V. All rights reserved.

AB - The significant advances in achiral catalysis using N-heterocyclic carbene (NHC) metal complexes have prompted intense investigation of chiral NHC derivatives for use in asymmetric catalysis in recent years. Discovery of new chiral NHC catalysts is supported by the development of synthetic routes to chiral NHC ligands and their metal complexes. Here routes to chiral NHC ligands derived principally from chiral diamines will be outlined and metal complex structures described in the context of application to asymmetric catalysis. Emphasis will be placed on palladium and copper catalysed asymmetric alkylations that serve to illustrate the potential and some limitations of NHC-based asymmetric catalysts. (c) 2006 Elsevier B.V. All rights reserved.

KW - N-heterocyclic carbenes

KW - catalysis

KW - chirality

KW - alkylation

KW - palladium

KW - copper

KW - CATALYZED CONJUGATE ADDITION

KW - ALLYLIC SUBSTITUTION-REACTION

KW - ALKOXY-NHC LIGANDS

KW - PALLADIUM(II) COMPLEXES

KW - OLEFIN METATHESIS

KW - RHODIUM COMPLEXES

KW - GRIGNARD-REAGENTS

KW - EFFICIENT

KW - REACTIVITY

KW - HYDROSILYLATION

U2 - 10.1016/j.ccr.2006.08.003

DO - 10.1016/j.ccr.2006.08.003

M3 - Article

SN - 0010-8545

VL - 251

SP - 702

EP - 717

JO - COORDINATION CHEMISTRY REVIEWS

JF - COORDINATION CHEMISTRY REVIEWS

IS - 5-6

ER -