Development of chiral heteroleptic magnesium amides; asymmetric deprotonations mediated by six-membered metallocyclic amidomagnesium naphtholates

Emma L. Carswell; William J Kerr; Duncan McArthur; Marek Pazicky; Allan Watson

doi:10.1016/j.tet.2014.06.052

Development of chiral heteroleptic magnesium amides; asymmetric deprotonations mediated by six-membered metallocyclic amidomagnesium naphtholates

Emma L. Carswell, William J Kerr, Duncan McArthur, Marek Pazicky, Allan Watson

School of Chemistry

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

5 Citations (Scopus)

Abstract

A series of enantioenriched six-membered metallocyclic amidomagnesium naphtholates were prepared and used to probe the structure-reactivity/selectivity relationships of heteroleptic magnesium base complexes within asymmetric deprotonation reactions. An effective complex was identified and applied within enantioselective enolisation processes, delivering good levels of enantioselectivity and also revealing key structural requirements for achieving such selectivity.

Original language	English
Pages (from-to)	7344-7349
Number of pages	6
Journal	Tetrahedron
Volume	70
Issue number	40
DOIs	https://doi.org/10.1016/j.tet.2014.06.052
Publication status	Published - 7 Oct 2014

Keywords

enantioselective deprotonation
heteroleptic magnesium bases
enolate
asymmetric synthesis
amidonaphtholate

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10.1016/j.tet.2014.06.052

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title = "Development of chiral heteroleptic magnesium amides; asymmetric deprotonations mediated by six-membered metallocyclic amidomagnesium naphtholates",

abstract = "A series of enantioenriched six-membered metallocyclic amidomagnesium naphtholates were prepared and used to probe the structure-reactivity/selectivity relationships of heteroleptic magnesium base complexes within asymmetric deprotonation reactions. An effective complex was identified and applied within enantioselective enolisation processes, delivering good levels of enantioselectivity and also revealing key structural requirements for achieving such selectivity.",

keywords = "enantioselective deprotonation, heteroleptic magnesium bases, enolate, asymmetric synthesis, amidonaphtholate",

author = "Carswell, {Emma L.} and Kerr, {William J} and Duncan McArthur and Marek Pazicky and Allan Watson",

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TY - JOUR

T1 - Development of chiral heteroleptic magnesium amides; asymmetric deprotonations mediated by six-membered metallocyclic amidomagnesium naphtholates

AU - Carswell, Emma L.

AU - Kerr, William J

AU - McArthur, Duncan

AU - Pazicky, Marek

AU - Watson, Allan

PY - 2014/10/7

Y1 - 2014/10/7

N2 - A series of enantioenriched six-membered metallocyclic amidomagnesium naphtholates were prepared and used to probe the structure-reactivity/selectivity relationships of heteroleptic magnesium base complexes within asymmetric deprotonation reactions. An effective complex was identified and applied within enantioselective enolisation processes, delivering good levels of enantioselectivity and also revealing key structural requirements for achieving such selectivity.

AB - A series of enantioenriched six-membered metallocyclic amidomagnesium naphtholates were prepared and used to probe the structure-reactivity/selectivity relationships of heteroleptic magnesium base complexes within asymmetric deprotonation reactions. An effective complex was identified and applied within enantioselective enolisation processes, delivering good levels of enantioselectivity and also revealing key structural requirements for achieving such selectivity.

KW - enantioselective deprotonation

KW - heteroleptic magnesium bases

KW - enolate

KW - asymmetric synthesis

KW - amidonaphtholate

U2 - 10.1016/j.tet.2014.06.052

DO - 10.1016/j.tet.2014.06.052

M3 - Article

SN - 0040-4020

VL - 70

SP - 7344

EP - 7349

JO - Tetrahedron

JF - Tetrahedron

IS - 40

ER -

Development of chiral heteroleptic magnesium amides; asymmetric deprotonations mediated by six-membered metallocyclic amidomagnesium naphtholates

Abstract

Keywords

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