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

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

SDG 12 Responsible Consumption and Production

Keywords

copper

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10.1016/S0957-4166(98)00240-7

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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",

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

language = "English",

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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/

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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

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