First Examples of Improved Catalytic Asymmetric C-C Bond Formation Using the Monodentate Ligand Combination Approach

Ate Duursma; Rob Hoen; Julia Schuppan; Ron Hulst; Adriaan J. Minnaard; Bernard Feringa

doi:10.1002/chin.200351028

First Examples of Improved Catalytic Asymmetric C-C Bond Formation Using the Monodentate Ligand Combination Approach

Ate Duursma
, Rob Hoen
, Julia Schuppan
, Ron Hulst
, Adriaan J. Minnaard
, Bernard Feringa

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

132 Citations (Scopus)

815 Downloads (Pure)

Abstract

Using a combination of chiral monodentate phosphoramidite ligands in the rhodium-catalyzed conjugate addition of boronic acids to three different substrates, we have shown for the first time that the ligand combination approach is applicable for C-C bond formation. Chiral catalysts based on hetero-combinations of ligands are found to be more effective than the homo-combinations. 31P NMR experiments show that the hetero-combinations are formed in excess over the homo-combinations.

Original language	English
Pages (from-to)	3111-3113
Number of pages	3
Journal	ChemInform
Volume	34
Issue number	51
DOIs	https://doi.org/10.1002/chin.200351028
Publication status	Published - 21-Aug-2003

Keywords

CONJUGATE ADDITION
ARYLBORONIC ACIDS
ORGANOBORONIC ACIDS
ALPHA,BETA-UNSATURATED ESTERS
1,4-ADDITION
PHOSPHORAMIDITES
HYDROGENATION
REAGENTS
NITROALKENES
DERIVATIVES

Access to Document

10.1002/chin.200351028

2003OrgLettDuursmaSupp.pdfFinal publisher's version, 38.1 KB
2003OrgLettDuursma.pdfFinal publisher's version, 62.3 KB

Handle.net

Persistent link

Cite this

@article{108caeee8d424e7ea5c8077826b0948d,

title = "First Examples of Improved Catalytic Asymmetric C-C Bond Formation Using the Monodentate Ligand Combination Approach",

abstract = "Using a combination of chiral monodentate phosphoramidite ligands in the rhodium-catalyzed conjugate addition of boronic acids to three different substrates, we have shown for the first time that the ligand combination approach is applicable for C-C bond formation. Chiral catalysts based on hetero-combinations of ligands are found to be more effective than the homo-combinations. 31P NMR experiments show that the hetero-combinations are formed in excess over the homo-combinations.",

keywords = "CONJUGATE ADDITION, ARYLBORONIC ACIDS, ORGANOBORONIC ACIDS, ALPHA,BETA-UNSATURATED ESTERS, 1,4-ADDITION, PHOSPHORAMIDITES, HYDROGENATION, REAGENTS, NITROALKENES, DERIVATIVES",

author = "Ate Duursma and Rob Hoen and Julia Schuppan and Ron Hulst and Minnaard, \{Adriaan J.\} and Bernard Feringa",

note = "Relation: http://www.rug.nl/scheikunde/ date\_submitted:2005 Rights: University of Groningen. Stratingh Institute",

year = "2003",

month = aug,

day = "21",

doi = "10.1002/chin.200351028",

language = "English",

volume = "34",

pages = "3111--3113",

journal = "ChemInform",

number = "51",

}

TY - JOUR

T1 - First Examples of Improved Catalytic Asymmetric C-C Bond Formation Using the Monodentate Ligand Combination Approach

AU - Duursma, Ate

AU - Hoen, Rob

AU - Schuppan, Julia

AU - Hulst, Ron

AU - Minnaard, Adriaan J.

AU - Feringa, Bernard

N1 - Relation: http://www.rug.nl/scheikunde/ date_submitted:2005 Rights: University of Groningen. Stratingh Institute

PY - 2003/8/21

Y1 - 2003/8/21

N2 - Using a combination of chiral monodentate phosphoramidite ligands in the rhodium-catalyzed conjugate addition of boronic acids to three different substrates, we have shown for the first time that the ligand combination approach is applicable for C-C bond formation. Chiral catalysts based on hetero-combinations of ligands are found to be more effective than the homo-combinations. 31P NMR experiments show that the hetero-combinations are formed in excess over the homo-combinations.

AB - Using a combination of chiral monodentate phosphoramidite ligands in the rhodium-catalyzed conjugate addition of boronic acids to three different substrates, we have shown for the first time that the ligand combination approach is applicable for C-C bond formation. Chiral catalysts based on hetero-combinations of ligands are found to be more effective than the homo-combinations. 31P NMR experiments show that the hetero-combinations are formed in excess over the homo-combinations.

KW - CONJUGATE ADDITION

KW - ARYLBORONIC ACIDS

KW - ORGANOBORONIC ACIDS

KW - ALPHA,BETA-UNSATURATED ESTERS

KW - 1,4-ADDITION

KW - PHOSPHORAMIDITES

KW - HYDROGENATION

KW - REAGENTS

KW - NITROALKENES

KW - DERIVATIVES

U2 - 10.1002/chin.200351028

DO - 10.1002/chin.200351028

M3 - Article

VL - 34

SP - 3111

EP - 3113

JO - ChemInform

JF - ChemInform

IS - 51

ER -

First Examples of Improved Catalytic Asymmetric C-C Bond Formation Using the Monodentate Ligand Combination Approach

Abstract

Keywords

Access to Document

Handle.net

Fingerprint

Cite this