Copper-catalyzed enantioselective conjugate addition of organometallic reagents to acyclic dienones

Radovan Sebesta; M. Gabriella Pizzuti; Adriaan J. Minnaard; Ben L. Feringa; Radovan Šebesta

doi:10.1002/adsc.200600272

Copper-catalyzed enantioselective conjugate addition of organometallic reagents to acyclic dienones

Radovan Sebesta, M. Gabriella Pizzuti, Adriaan J. Minnaard^*, Ben L. Feringa, Radovan Šebesta

^*Corresponding author for this work

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

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Abstract

The enantioselective, copper/phosphoramidite-catalyzed 1,4-addition of dialkylzinc reagents to acyclic dienones is described. The products of this reaction, obtained with enantioselectivities of up to 95%, can be further functionalized by a second conjugate addition, or employed in an enolate trapping, ring-closing metathesis protocol.

Original language	English
Pages (from-to)	1931-1937
Number of pages	7
Journal	Advanced Synthesis & Catalysis
Volume	349
Issue number	11-12
DOIs	https://doi.org/10.1002/adsc.200600272
Publication status	Published - Aug-2007

Keywords

conjugate addition
copper
dialkylzinc reagents
dienones
enantioselectivity
phosphoramidites
PHOSPHITE-PYRIDINE LIGANDS
DIALKYLZINC REAGENTS
PHOSPHORAMIDITE LIGANDS
ASYMMETRIC-SYNTHESIS
ORGANOZINC REAGENTS
GRIGNARD-REAGENTS
ALIPHATIC ENONES
DIETHYLZINC
COMPLEXES
METATHESIS

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@article{2cc8342f90c7468ca328403a29b8aff3,

title = "Copper-catalyzed enantioselective conjugate addition of organometallic reagents to acyclic dienones",

abstract = "The enantioselective, copper/phosphoramidite-catalyzed 1,4-addition of dialkylzinc reagents to acyclic dienones is described. The products of this reaction, obtained with enantioselectivities of up to 95\%, can be further functionalized by a second conjugate addition, or employed in an enolate trapping, ring-closing metathesis protocol.",

keywords = "conjugate addition, copper, dialkylzinc reagents, dienones, enantioselectivity, phosphoramidites, PHOSPHITE-PYRIDINE LIGANDS, DIALKYLZINC REAGENTS, PHOSPHORAMIDITE LIGANDS, ASYMMETRIC-SYNTHESIS, ORGANOZINC REAGENTS, GRIGNARD-REAGENTS, ALIPHATIC ENONES, DIETHYLZINC, COMPLEXES, METATHESIS",

author = "Radovan Sebesta and Pizzuti, \{M. Gabriella\} and Minnaard, \{Adriaan J.\} and Feringa, \{Ben L.\} and Radovan {\v S}ebesta",

note = "Cited By (since 1996): 7",

year = "2007",

month = aug,

doi = "10.1002/adsc.200600272",

language = "English",

volume = "349",

pages = "1931--1937",

journal = "Advanced Synthesis \& Catalysis",

issn = "1615-4150",

publisher = "WILEY-V C H VERLAG GMBH",

number = "11-12",

}

TY - JOUR

T1 - Copper-catalyzed enantioselective conjugate addition of organometallic reagents to acyclic dienones

AU - Sebesta, Radovan

AU - Pizzuti, M. Gabriella

AU - Minnaard, Adriaan J.

AU - Feringa, Ben L.

AU - Šebesta, Radovan

N1 - Cited By (since 1996): 7

PY - 2007/8

Y1 - 2007/8

N2 - The enantioselective, copper/phosphoramidite-catalyzed 1,4-addition of dialkylzinc reagents to acyclic dienones is described. The products of this reaction, obtained with enantioselectivities of up to 95%, can be further functionalized by a second conjugate addition, or employed in an enolate trapping, ring-closing metathesis protocol.

AB - The enantioselective, copper/phosphoramidite-catalyzed 1,4-addition of dialkylzinc reagents to acyclic dienones is described. The products of this reaction, obtained with enantioselectivities of up to 95%, can be further functionalized by a second conjugate addition, or employed in an enolate trapping, ring-closing metathesis protocol.

KW - conjugate addition

KW - copper

KW - dialkylzinc reagents

KW - dienones

KW - enantioselectivity

KW - phosphoramidites

KW - PHOSPHITE-PYRIDINE LIGANDS

KW - DIALKYLZINC REAGENTS

KW - PHOSPHORAMIDITE LIGANDS

KW - ASYMMETRIC-SYNTHESIS

KW - ORGANOZINC REAGENTS

KW - GRIGNARD-REAGENTS

KW - ALIPHATIC ENONES

KW - DIETHYLZINC

KW - COMPLEXES

KW - METATHESIS

U2 - 10.1002/adsc.200600272

DO - 10.1002/adsc.200600272

M3 - Article

SN - 1615-4150

VL - 349

SP - 1931

EP - 1937

JO - Advanced Synthesis & Catalysis

JF - Advanced Synthesis & Catalysis

IS - 11-12

ER -

Copper-catalyzed enantioselective conjugate addition of organometallic reagents to acyclic dienones

Abstract

Keywords

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