Unexpected enhancement of enantioselectivity in copper(II) catalyzed conjugate addition of diethylzinc to cyclic enones with novel TADDOL phosphorus amidite ligands

Erik Keller; Jochen Maurer; Robert Naasz; Thomas Schader; Auke Meetsma; Ben L. Feringa

doi:10.1016/S0957-4166(98)00240-7

Unexpected enhancement of enantioselectivity in copper(II) catalyzed conjugate addition of diethylzinc to cyclic enones with novel TADDOL phosphorus amidite ligands

Erik Keller, Jochen Maurer, Robert Naasz, Thomas Schader, Auke Meetsma, Ben L. Feringa

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

Abstract

The copper(II) catalyzed enantioselective 1,4-addition reactions of diethylzinc to cyclic enones in the presence of novel phosphorus amidite ligands, easily prepared from α,α,α',α'-tetraphenyl-2,2'-dimethyl-1,3- dioxolane-4,5-dimethanol (TADDOL) derivatives, resulted in e.e.s up to 71% for cyclohexenone and up to 62% for cyclopentenone. A remarkable enhancement of enantioselectivity was observed upon the addition of powdered molecular sieves to the reaction mixture.

Original language	English
Pages (from-to)	2409-2413
Journal	Tetrahedron: asymmetry
Volume	9
Issue number	14
DOIs	https://doi.org/10.1016/S0957-4166(98)00240-7
Publication status	Published - 17 Jul 1998

Keywords

copper

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1016/S0957-4166(98)00240-7

Cite this

@article{2627a255367449ad9647058e2b6b8e4d,

title = "Unexpected enhancement of enantioselectivity in copper(II) catalyzed conjugate addition of diethylzinc to cyclic enones with novel TADDOL phosphorus amidite ligands",

abstract = "The copper(II) catalyzed enantioselective 1,4-addition reactions of diethylzinc to cyclic enones in the presence of novel phosphorus amidite ligands, easily prepared from α,α,α',α'-tetraphenyl-2,2'-dimethyl-1,3- dioxolane-4,5-dimethanol (TADDOL) derivatives, resulted in e.e.s up to 71% for cyclohexenone and up to 62% for cyclopentenone. A remarkable enhancement of enantioselectivity was observed upon the addition of powdered molecular sieves to the reaction mixture.",

keywords = "copper, koper, katalyse",

author = "Erik Keller and Jochen Maurer and Robert Naasz and Thomas Schader and Auke Meetsma and Feringa, {Ben L.}",

year = "1998",

month = jul,

day = "17",

doi = "10.1016/S0957-4166(98)00240-7",

language = "English",

volume = "9",

pages = "2409--2413",

journal = "Tetrahedron: asymmetry",

issn = "0957-4166",

publisher = "Elsevier Limited",

number = "14",

}

TY - JOUR

T1 - Unexpected enhancement of enantioselectivity in copper(II) catalyzed conjugate addition of diethylzinc to cyclic enones with novel TADDOL phosphorus amidite ligands

AU - Keller, Erik

AU - Maurer, Jochen

AU - Naasz, Robert

AU - Schader, Thomas

AU - Meetsma, Auke

AU - Feringa, Ben L.

PY - 1998/7/17

Y1 - 1998/7/17

N2 - The copper(II) catalyzed enantioselective 1,4-addition reactions of diethylzinc to cyclic enones in the presence of novel phosphorus amidite ligands, easily prepared from α,α,α',α'-tetraphenyl-2,2'-dimethyl-1,3- dioxolane-4,5-dimethanol (TADDOL) derivatives, resulted in e.e.s up to 71% for cyclohexenone and up to 62% for cyclopentenone. A remarkable enhancement of enantioselectivity was observed upon the addition of powdered molecular sieves to the reaction mixture.

AB - The copper(II) catalyzed enantioselective 1,4-addition reactions of diethylzinc to cyclic enones in the presence of novel phosphorus amidite ligands, easily prepared from α,α,α',α'-tetraphenyl-2,2'-dimethyl-1,3- dioxolane-4,5-dimethanol (TADDOL) derivatives, resulted in e.e.s up to 71% for cyclohexenone and up to 62% for cyclopentenone. A remarkable enhancement of enantioselectivity was observed upon the addition of powdered molecular sieves to the reaction mixture.

KW - copper

KW - koper

KW - katalyse

UR - https://www.mendeley.com/catalogue/557c4106-519f-35ca-be12-ec2252306bcb/

U2 - 10.1016/S0957-4166(98)00240-7

DO - 10.1016/S0957-4166(98)00240-7

M3 - Article

SN - 0957-4166

VL - 9

SP - 2409

EP - 2413

JO - Tetrahedron: asymmetry

JF - Tetrahedron: asymmetry

IS - 14

ER -

Unexpected enhancement of enantioselectivity in copper(II) catalyzed conjugate addition of diethylzinc to cyclic enones with novel TADDOL phosphorus amidite ligands

Abstract

Keywords

UN SDGs

Access to Document

Other files and links

Fingerprint

Cite this