An insoluble polymer-bound phosphoramidite for the copper-catalysed enantioselective 1,4-addition of ZnEt2 to 2-cyclohexenone

A Mandoli; M Calamante; BL Feringa; P Salvadori

doi:10.1016/j.tetasy.2003.08.004

An insoluble polymer-bound phosphoramidite for the copper-catalysed enantioselective 1,4-addition of ZnEt2 to 2-cyclohexenone

A Mandoli, M Calamante, BL Feringa, P Salvadori^*

^*Corresponding author for this work

Synthetic Organic Chemistry

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

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Abstract

The preparation of a chiral phosphoramidite ligand anchored to a Merrifield resin has been studied and its use in the copper-catalysed heterogeneous enantioselective conjugate addition of ZnEt2 to 2-cyclohexenone investigated. The insoluble polymer bound ligand could be recovered quantitatively by filtration, affording e.e. values in the range 65-84%, in the course of successive recycle runs. (C) 2003 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	3647-3650
Number of pages	4
Journal	Tetrahedron-Asymmetry
Volume	14
Issue number	23
DOIs	https://doi.org/10.1016/j.tetasy.2003.08.004
Publication status	Published - 28-Nov-2003

Keywords

CONJUGATE ADDITION-REACTIONS
LIGANDS
COMPLEXES
HYDROGENATION
REAGENTS
ALKENES
ESTERS
IMINES

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title = "An insoluble polymer-bound phosphoramidite for the copper-catalysed enantioselective 1,4-addition of ZnEt2 to 2-cyclohexenone",

abstract = "The preparation of a chiral phosphoramidite ligand anchored to a Merrifield resin has been studied and its use in the copper-catalysed heterogeneous enantioselective conjugate addition of ZnEt2 to 2-cyclohexenone investigated. The insoluble polymer bound ligand could be recovered quantitatively by filtration, affording e.e. values in the range 65-84%, in the course of successive recycle runs. (C) 2003 Elsevier Ltd. All rights reserved.",

keywords = "CONJUGATE ADDITION-REACTIONS, LIGANDS, COMPLEXES, HYDROGENATION, REAGENTS, ALKENES, ESTERS, IMINES",

author = "A Mandoli and M Calamante and BL Feringa and P Salvadori",

year = "2003",

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day = "28",

doi = "10.1016/j.tetasy.2003.08.004",

language = "English",

volume = "14",

pages = "3647--3650",

journal = "Tetrahedron-Asymmetry",

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TY - JOUR

T1 - An insoluble polymer-bound phosphoramidite for the copper-catalysed enantioselective 1,4-addition of ZnEt2 to 2-cyclohexenone

AU - Mandoli, A

AU - Calamante, M

AU - Feringa, BL

AU - Salvadori, P

PY - 2003/11/28

Y1 - 2003/11/28

N2 - The preparation of a chiral phosphoramidite ligand anchored to a Merrifield resin has been studied and its use in the copper-catalysed heterogeneous enantioselective conjugate addition of ZnEt2 to 2-cyclohexenone investigated. The insoluble polymer bound ligand could be recovered quantitatively by filtration, affording e.e. values in the range 65-84%, in the course of successive recycle runs. (C) 2003 Elsevier Ltd. All rights reserved.

AB - The preparation of a chiral phosphoramidite ligand anchored to a Merrifield resin has been studied and its use in the copper-catalysed heterogeneous enantioselective conjugate addition of ZnEt2 to 2-cyclohexenone investigated. The insoluble polymer bound ligand could be recovered quantitatively by filtration, affording e.e. values in the range 65-84%, in the course of successive recycle runs. (C) 2003 Elsevier Ltd. All rights reserved.

KW - CONJUGATE ADDITION-REACTIONS

KW - LIGANDS

KW - COMPLEXES

KW - HYDROGENATION

KW - REAGENTS

KW - ALKENES

KW - ESTERS

KW - IMINES

U2 - 10.1016/j.tetasy.2003.08.004

DO - 10.1016/j.tetasy.2003.08.004

M3 - Article

SN - 0957-4166

VL - 14

SP - 3647

EP - 3650

JO - Tetrahedron-Asymmetry

JF - Tetrahedron-Asymmetry

IS - 23

ER -