1,2-aminothioethers derived from ephedrine and pseudoephedrine: Heterobidentate ligands for the palladium-catalysed asymmetric allylic substitution reaction

P. C. B. Bulman Page; H. Heaney; S. Reignier; G. A. Rassias

doi:10.1055/s-2003-36221

1,2-aminothioethers derived from ephedrine and pseudoephedrine: Heterobidentate ligands for the palladium-catalysed asymmetric allylic substitution reaction

P. C. B. Bulman Page
, H. Heaney
, S. Reignier
, G. A. Rassias

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

8 Citations (Scopus)

Abstract

Heterobidentate sulfide-tertiary amine ligands incorporating 1,2-aminothioethers derived from ephedrine and pseudoephedrine have been prepared and used successfully in the palladium-catalysed asymmetric allylic substitution reaction, giving ees of up to 89%. The stereoelectronic effects operating in the reactions are discussed.

Original language	English
Pages (from-to)	22-28
Number of pages	7
Journal	Synlett
Issue number	1
DOIs	https://doi.org/10.1055/s-2003-36221
Publication status	Published - 2003

Keywords

CHIRAL
ALKYLATION
LIGANDS
ENANTIOSELECTIVE CATALYSIS
ephedrine
heterobidentate ligands
NUCLEAR-MAGNETIC-RESONANCE
CHELATE LIGANDS
AMINATION
CONTAINING OXAZOLINE LIGANDS
METAL-COMPLEXES
allylic substitution
HYBRID LIGANDS
(ETA-3-ALLYL)PALLADIUM COMPLEXES

Access to Document

10.1055/s-2003-36221

Cite this

@article{ae411215c4b04bca804f62b14784d0bb,

title = "1,2-aminothioethers derived from ephedrine and pseudoephedrine: Heterobidentate ligands for the palladium-catalysed asymmetric allylic substitution reaction",

abstract = "Heterobidentate sulfide-tertiary amine ligands incorporating 1,2-aminothioethers derived from ephedrine and pseudoephedrine have been prepared and used successfully in the palladium-catalysed asymmetric allylic substitution reaction, giving ees of up to 89\%. The stereoelectronic effects operating in the reactions are discussed.",

keywords = "CHIRAL, ALKYLATION, LIGANDS, ENANTIOSELECTIVE CATALYSIS, ephedrine, heterobidentate ligands, NUCLEAR-MAGNETIC-RESONANCE, CHELATE LIGANDS, AMINATION, CONTAINING OXAZOLINE LIGANDS, METAL-COMPLEXES, allylic substitution, HYBRID LIGANDS, (ETA-3-ALLYL)PALLADIUM COMPLEXES",

author = "\{Bulman Page\}, \{P. C. B.\} and H. Heaney and S. Reignier and Rassias, \{G. A.\}",

year = "2003",

doi = "10.1055/s-2003-36221",

language = "English",

pages = "22--28",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "1",

}

TY - JOUR

T1 - 1,2-aminothioethers derived from ephedrine and pseudoephedrine: Heterobidentate ligands for the palladium-catalysed asymmetric allylic substitution reaction

AU - Bulman Page, P. C. B.

AU - Heaney, H.

AU - Reignier, S.

AU - Rassias, G. A.

PY - 2003

Y1 - 2003

N2 - Heterobidentate sulfide-tertiary amine ligands incorporating 1,2-aminothioethers derived from ephedrine and pseudoephedrine have been prepared and used successfully in the palladium-catalysed asymmetric allylic substitution reaction, giving ees of up to 89%. The stereoelectronic effects operating in the reactions are discussed.

AB - Heterobidentate sulfide-tertiary amine ligands incorporating 1,2-aminothioethers derived from ephedrine and pseudoephedrine have been prepared and used successfully in the palladium-catalysed asymmetric allylic substitution reaction, giving ees of up to 89%. The stereoelectronic effects operating in the reactions are discussed.

KW - CHIRAL

KW - ALKYLATION

KW - LIGANDS

KW - ENANTIOSELECTIVE CATALYSIS

KW - ephedrine

KW - heterobidentate ligands

KW - NUCLEAR-MAGNETIC-RESONANCE

KW - CHELATE LIGANDS

KW - AMINATION

KW - CONTAINING OXAZOLINE LIGANDS

KW - METAL-COMPLEXES

KW - allylic substitution

KW - HYBRID LIGANDS

KW - (ETA-3-ALLYL)PALLADIUM COMPLEXES

U2 - 10.1055/s-2003-36221

DO - 10.1055/s-2003-36221

M3 - Letter

SN - 0936-5214

SP - 22

EP - 28

JO - Synlett

JF - Synlett

IS - 1

ER -