Ligand's electronegativity controls the sense of enantioselectivity in BIFOP-X palladium-catalyzed allylic alkylations

Eric Brüllingen; Jörg-Martin Neudörfl; Bernd Goldfuss

doi:10.1039/c9nj02798j

Ligand's electronegativity controls the sense of enantioselectivity in BIFOP-X palladium-catalyzed allylic alkylations

New Journal of Chemistry ◽

10.1039/c9nj02798j ◽

2019 ◽

Vol 43 (39) ◽

pp. 15743-15753

Author(s):

Eric Brüllingen ◽

Jörg-Martin Neudörfl ◽

Bernd Goldfuss

Keyword(s):

Coupling Product ◽

Allylic Alkylations ◽

Palladium Catalyzed

Palladium-catalyzed allylic alkylations of Na(CH(CO2Me)2 with 1,3-diphenylallyl acetate, employing BIFOP-X (X = H, D, Cl, CN, N3) ligands, yield the C–C coupling product (up to 91% yield, 70% ee). A NBO effect reveals a change of stereochemistry.

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Enantioselective Palladium-Catalyzed Decarboxylative Allylic Alkylations

ChemInform ◽

10.1002/chin.200647251 ◽

2006 ◽

Vol 37 (47) ◽

Author(s):

Shu-Li You ◽

Li-Xin Dai

Keyword(s):

Allylic Alkylations ◽

Palladium Catalyzed

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Palladium-Catalyzed Allylic Alkylations as Versatile Tool for Amino Acid and Peptide Modifications

Synthesis ◽

10.1055/s-0033-1338477 ◽

2013 ◽

Vol 45 (11) ◽

pp. 1462-1468 ◽

Cited By ~ 16

Author(s):

Uli Kazmaier ◽

Anton Bayer ◽

Jan Deska

Keyword(s):

Amino Acid ◽

Allylic Alkylations ◽

Versatile Tool ◽

Palladium Catalyzed ◽

Peptide Modifications

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ChemInform Abstract: Palladium-Catalyzed Enantioselective Asymmetric Allylic Alkylations Using the Berens′ DIOP Analogue.

ChemInform ◽

10.1002/chin.200803026 ◽

2008 ◽

Vol 39 (3) ◽

Author(s):

Caroline S. Marques ◽

Anthony J. Burke

Keyword(s):

Allylic Alkylations ◽

Palladium Catalyzed

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ChemInform Abstract: PALLADIUM-CATALYZED ALLYLIC ALKYLATIONS OF ALLYLIC NITRO COMPOUNDS

Chemischer Informationsdienst ◽

10.1002/chin.198252152 ◽

1982 ◽

Vol 13 (52) ◽

Author(s):

N. ONO ◽

I. HAMAMOTO ◽

A. KAJI

Keyword(s):

Nitro Compounds ◽

Allylic Alkylations ◽

Palladium Catalyzed

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Cyclizations via Palladium-Catalyzed Allylic Alkylations[New Synthetic Methods(79)]

Angewandte Chemie International Edition in English ◽

10.1002/anie.198911731 ◽

1989 ◽

Vol 28 (9) ◽

pp. 1173-1192 ◽

Cited By ~ 217

Author(s):

Barry M. Trost

Keyword(s):

Synthetic Methods ◽

Allylic Alkylations ◽

Palladium Catalyzed

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ChemInform Abstract: A Modular Approach for Ligand Design for Asymmetric Allylic Alkylations via Enantioselective Palladium-Catalyzed Ionizations.

ChemInform ◽

10.1002/chin.199311153 ◽

2010 ◽

Vol 24 (11) ◽

pp. no-no

Author(s):

B. M. TROST ◽

D. L. VAN VRANKEN ◽

C. BINGEL

Keyword(s):

Ligand Design ◽

Modular Approach ◽

Allylic Alkylations ◽

Palladium Catalyzed

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ChemInform Abstract: New Chiral o-(Phosphinoamido)phenyl Sulfoxide Ligands in Palladium-Catalyzed Asymmetric Allylic Alkylations.

ChemInform ◽

10.1002/chin.199848026 ◽

2010 ◽

Vol 29 (48) ◽

pp. no-no

Author(s):

K. HIROI ◽

Y. SUZUKI

Keyword(s):

Allylic Alkylations ◽

Palladium Catalyzed

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Palladium-Catalyzed Allylic Alkylations of Nonstabilized Enolates

ChemInform ◽

10.1002/chin.200333266 ◽

2003 ◽

Vol 34 (33) ◽

Author(s):

U. Kazmaier

Keyword(s):

Allylic Alkylations ◽

Palladium Catalyzed

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Ligand-Controlled Palladium-Catalyzed Asymmetric Allylic Alkylations

Synfacts ◽

10.1055/s-0028-1083428 ◽

2008 ◽

Vol 2008 (11) ◽

pp. 1183-1183

Author(s):

B. Trost ◽

J. Xu ◽

T. Schmidt

Keyword(s):

Allylic Alkylations ◽

Palladium Catalyzed

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Regioselective Palladium-Catalyzed Allylic Alkylations.

ChemInform ◽

10.1002/chin.200519084 ◽

2005 ◽

Vol 36 (19) ◽

Author(s):

Ying Dong ◽

Paul Teesdale-Spittle ◽

John O. Hoberg

Keyword(s):

Allylic Alkylations ◽

Palladium Catalyzed

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