Novel polymer-bound aminoalcohol ligands for the asymmetric addition of diethylzinc to aldehydes

P. C. B. Bulman Page; S. M. Allin; S. J. Dilly; B. R. Buckley

doi:10.1080/00397910701356553

Novel polymer-bound aminoalcohol ligands for the asymmetric addition of diethylzinc to aldehydes

P. C. B. Bulman Page, S. M. Allin, S. J. Dilly, B. R. Buckley

Chemistry of Materials and Catalysis

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

7 Citations (Scopus)

Abstract

The synthesis of several novel polymer-supported aziridine- containing aminoalcohol chiral ligands has been accomplished, and the polymers have been used as ligands for the catalytic asymmetric addition of diethylzinc to benzaldehyde, giving up to 89% ee. Incorporation onto a polymer support prevents the variation of ee with time that is observed in reactions of one unsupported ligand, perhaps as a result of site isolation of the ligand within the polymer, preventing cooperative effects.

Original language	English
Pages (from-to)	2019-2030
Number of pages	12
Journal	Synthetic Communications
Volume	37
Issue number	12
DOIs	https://doi.org/10.1080/00397910701356553
Publication status	Published - 2007

Keywords

CATALYSTS
ALKYLATION
aminoalcohol
ligand
DIALKYLZINCS
addition
ALCOHOLS
aldehyde
BENZALDEHYDE
asymmetric dialkyl zinc
CARBONYL-COMPOUNDS
ENANTIOSELECTIVE ADDITION
SELF

Access to Document

10.1080/00397910701356553

Cite this

@article{23dfbcccc0c74b98bcbcf42c85a04550,

title = "Novel polymer-bound aminoalcohol ligands for the asymmetric addition of diethylzinc to aldehydes",

abstract = "The synthesis of several novel polymer-supported aziridine- containing aminoalcohol chiral ligands has been accomplished, and the polymers have been used as ligands for the catalytic asymmetric addition of diethylzinc to benzaldehyde, giving up to 89% ee. Incorporation onto a polymer support prevents the variation of ee with time that is observed in reactions of one unsupported ligand, perhaps as a result of site isolation of the ligand within the polymer, preventing cooperative effects.",

keywords = "CATALYSTS, ALKYLATION, aminoalcohol, ligand, DIALKYLZINCS, addition, ALCOHOLS, aldehyde, BENZALDEHYDE, asymmetric dialkyl zinc, CARBONYL-COMPOUNDS, ENANTIOSELECTIVE ADDITION, SELF",

author = "{Bulman Page}, {P. C. B.} and Allin, {S. M.} and Dilly, {S. J.} and Buckley, {B. R.}",

year = "2007",

doi = "10.1080/00397910701356553",

language = "English",

volume = "37",

pages = "2019--2030",

journal = "Synthetic Communications",

issn = "0039-7911",

publisher = "Taylor and Francis",

number = "12",

}

TY - JOUR

T1 - Novel polymer-bound aminoalcohol ligands for the asymmetric addition of diethylzinc to aldehydes

AU - Bulman Page, P. C. B.

AU - Allin, S. M.

AU - Dilly, S. J.

AU - Buckley, B. R.

PY - 2007

Y1 - 2007

N2 - The synthesis of several novel polymer-supported aziridine- containing aminoalcohol chiral ligands has been accomplished, and the polymers have been used as ligands for the catalytic asymmetric addition of diethylzinc to benzaldehyde, giving up to 89% ee. Incorporation onto a polymer support prevents the variation of ee with time that is observed in reactions of one unsupported ligand, perhaps as a result of site isolation of the ligand within the polymer, preventing cooperative effects.

AB - The synthesis of several novel polymer-supported aziridine- containing aminoalcohol chiral ligands has been accomplished, and the polymers have been used as ligands for the catalytic asymmetric addition of diethylzinc to benzaldehyde, giving up to 89% ee. Incorporation onto a polymer support prevents the variation of ee with time that is observed in reactions of one unsupported ligand, perhaps as a result of site isolation of the ligand within the polymer, preventing cooperative effects.

KW - CATALYSTS

KW - ALKYLATION

KW - aminoalcohol

KW - ligand

KW - DIALKYLZINCS

KW - addition

KW - ALCOHOLS

KW - aldehyde

KW - BENZALDEHYDE

KW - asymmetric dialkyl zinc

KW - CARBONYL-COMPOUNDS

KW - ENANTIOSELECTIVE ADDITION

KW - SELF

U2 - 10.1080/00397910701356553

DO - 10.1080/00397910701356553

M3 - Article

VL - 37

SP - 2019

EP - 2030

JO - Synthetic Communications

JF - Synthetic Communications

SN - 0039-7911

IS - 12

ER -