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

Onderzoeksoutput: Article › Academic › peer review

Samenvatting

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.

Originele taal-2	English
Pagina's (van-tot)	2409-2413
Tijdschrift	Tetrahedron: asymmetry
Volume	9
Nummer van het tijdschrift	14
DOI's	https://doi.org/10.1016/S0957-4166(98)00240-7
Status	Published - 17 jul. 1998

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Keywords

koper
katalyse

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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",

month = jul,

day = "17",

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

language = "English",

volume = "9",

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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/

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

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Keywords

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