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New Journal of Chemistry
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ARTICLE
X.Ray Crystallographic Studies, NMR Investigations, and Ab
Journal Name
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Initio/DFT Calculations. Chem. Eur. J. 2002, 8, 3103-3114; (g)
P. von Matt, A. Pfaltz, Chiral Phosphinoaryldihydrooxazoles
as Ligands in Asymmetric Catalysis: Pd-Catalyzed Allylic
Substitution. Angew. Chem. Int. Ed. 1993, 32, 566-568;
Chirale Phosphinoarylhydrooxazole als Liganden in der
DOI: 10.1039/C9NJ02798J
F. Rominger, H. Urtel, Chiral Modular n-Butyllithium
Aggregates: nBuLi Complexes with Anisyl Fencholates. Chem.
Eur. J. 2001, 7, 4456-4464; (m) B. Goldfuss, Organolithiums in
Enantioselective Additions to n* and σ* Carbon-Oxygen
Electrophiles. Synthesis 2005, 2271-2280; (n) B. Goldfuss, M.
Steigelmann, T. Löschmann, G. Schilling, F. Rominger, A
Dispensable Methoxy Group? Phenyl Fencholate as a Chiral
Modifier of n-Butyllithium. Chem. Eur. J. 2005, 11, 4019-
4023; (o) F. Soki, J.-M. Neudörfl, B. Goldfuss, Homo- vs.
heterometallic organolithium fencholates: Structures and
selectivities. J. Organomet. Chem. 2008, 693, 2139-2146; (p)
M. Leven, N. E. Schlörer, J.-M. Neudörfl, B. Goldfuss, Control
of Enantioselectivity with Felxible Biaryl Axes: Terpene-Based
Alkylzinc Catalysts in Enatioselective Dialkylzinc Additions.
Chem. Eur. J. 2010, 16, 13443-13449; (q) M. Leven, D. Müller,
B. Goldfuss, Enantioselective Alkynylation of Aromatic
Aldehydes: Pyridyl Phenylene Terpeneol Catalysts with
Flexible Biaryl Axes. Synlett 2011, 2505-2508; (r) A. Gliga, H.
Klare, M. Schumacher, F. Soki, J.-M. Neudörfl, B. Goldfuss,
New Umpolung Catalysts: Reactivity and Selectivity of
Terpenol-Based Lithium Phosphonates in Enantioselective
Benzoin-Type Couplings. Eur. J. Org. Chem. 2011, 256-263;
(s) V. Grote, J.-M. Neudörfl, B. Goldfuss, Enantiopure Methyl-
Phenyllithium: Mixed (Carb-)Anionic Anisyl Fencholate-
Aggregates. Organomet. 2019, 38, 771-779; (t) F. Fox, J.-M.
Neudörfl, B. Goldfuss, Silanediol versus chlorosilanol:
hydrolyes and hydrogen-bonding catalyses with fenchole-
based silanes. Beilstein J. Org. Chem. 2019, 15, 167-186.
(a) B. Goldfuss, T. Kop-Weiershausen, J. Lex, J.-M. Neudörfl,
An exceptional P-H phosphonite: Biphenyl- 2,2‘-
bisfenchylchlorophosphite and derived ligands (BIFOPs) in
enatioselective copper- catalyzed 1,4-additions. Beilstein J.
Org. Chem. 2005, 1, 6-10; (b) B. Goldfuss, T. Löschmann, T.
Kop-Weiershausen, J.-M. Neudörfl, F. Rominger, A superior
P-H phosphonite: Asymmetric allylic substitutions with
fenchol-based palladium catalysts. Beilst. J. Org. Chem. 2006,
2, 7-11.
asymmetrischen
Katalyse:
Pd-katalysierte
allylische
Substitution. Angew. Chem. 1993, 105, 614-615; (h) J. Sprinz,
G. Helmchen, Phosphinoaryl- and phosphinoalkyloxazolines
as new chiral ligands for enantioselective catalysis: Very high
enantioselectivity in palladium catalyzed allylic substitutions.
Tetrahedron Lett. 1993, 34, 1769-1772; (i) J. G. Dawson, C. G.
Frost, S. J. Coote, J. M. J. Williams, Asymmetric palladium
catalysed allylic substitution using phosphorus containing
oxazoline ligands. Tetrahedron Lett. 1993, 34, 3149-3150; (j)
J. M. J Williams, The Ups and Downs of Allylpalladium
Complexes in Catalysis. Synlett 1996, 705-710.
B. Goldfuss, T. Löschmann, F. Rominger, Ligand Bite Governs
Enantioselectivity: Electronic and Steric Control in Pd-
Catalyzed Allylic Alkylations by Molecular Fenchyl
Phosphinites (FENOPs). Chem. Eur. J. 2004, 10, 5422-5427.
E. Brüllingen, J.-M. Neudörfl, B. Goldfuss, Enantioselective
Cu-catalyzed 1,4-additions of organozinc and Grignard
reagents to enones: exceptional performance of the hydrido-
phosphite-ligand BIFOP-H. New J. Chem. 2019, 43, 4787-
4799.
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(a) W. Neugebauer, A. J. Kos, P. V. R. Schleyer, Regioselektive
dimetallierung von aromaten. Bequemer zugang zu 2,2‘-
disubstituierten biphenylderivaten. J. Organomet. Chem.
1982, 228, 107-118; (b) B. Goldfuss, E. Eisenträger, Chiral
ligand induced distortions: the origin of pyramidal three-
coordinated lithium ions in the X-ray crystal structure of
Lithium (1R,2R,4S)-exo-2-[o-(dimethylaminomethyl)phenyl]-
1,3,3-trimethylbicyclo[2.2.1]heptan-endo-2-olate. Aust. J.
Chem. 2000, 53, 209-212; (c) B. Goldfuss, T. Löschmann, F.
Rominger, Phosphinofenchol or Metastable Phosphorane?
Phosphorus Derivatives of Fenchol. Chem. Eur. J. 2001, 7,
2028-2033; (d) F. Soki, J.-M. Neudörfl, B. Goldfuss, Surprising
fenchone induced cyclization: synthesis of the new chiral diol
biphenyl-2,2’-sulfone-3,3’-bisfenchol (BISFOL). Tetrahedron
2005, 61, 10449-10453; (e) D. Lange, J.-M. Neudörfl, B.
Goldfuss, New chiral lithium aluminum hydrides based on
biphenyl-2,2‘-bisfenchol (BIFOL): structural analyses and
enantioselective reductions of aryl ketones. Tetrahedron
2006, 62, 3704-3709; (f) B. Goldfuss, S. I. Khan, K. N. Houk,
Chiral Complexes with n-Butyllithium and Methylzinc: X-ray
Crystal Structures of Lithium and Zinc (1R,2R,4S)-2-endo-
Oxido-2-eco-(o-methoxyphenyl)-1,3,3-
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R. Blanco-Trillo, M. Leven, J.-M. Neudörfl, B. Goldfuss,
Electronegativity Governs Enantioselectivity: Alkyl-Aryl
Cross-Coupling with Fenchol-Based Palladium-Phosphorus
Halide Catalysts. Adv. Synth. Catal. 2012, 354, 1451-1465.
(a) M. Aufiero, R. Gilmour, Informing Molecular Design by
Stereoelectronic Theory: The Fluorine Gauche Effect in
Catalysis. Acc. Chem. Res. 2018, 51, 1701-1710; (b) C.
Thiehoff, Y. P. Rey, R. Gilmour, The Fluorine Gauche Effect: A
Brief History. Isr. J. Chem. 2017, 57, 92-100; (c) K. A. Lee, D. L.
Silverio, S. Forker, D. W. Robbins, F. Haeffner, F. W. van der
Mei, A. H. Hoveyda, Catalytic enantioselective addition of
organoboron reagents to fluoroketones controlled by
electrostatic interactions. Nat. Chem. 2016, 8, 768-777; (d) C.
Thiehoff, M. C. Holland, C. Daniliuc, K. N. Houk, R. Gilmour,
Can acyclic conformational control be achieved via a sulfur-
fluorine gauche effect? Chem. Sci. 2015, 6, 3565-3571; (e) L.
E. Zimmer, C. Sparr, R. Gilmour, Fluorine Conformational
Effects in Organocatalysis: An Emerging Strategy for
Molecular Design. Angew. Chem. Int. Ed. 2011, 50, 11860-
11871; (f) D. Cahard, V. Bizet, The influence of fluorine in
asymmetric catalysis. Chem. Soc. Rev. 2014, 43, 135-147; (g)
V. Bizet, D. Cahard, Fluorine as a Control Element in
Asymmetric Synthesis. Chimia 2014, 68, 378-381.
trimethylbicyclo[2.2.1]heptanes. Organometallics 1999, 18,
2927-2929; (g) B. Goldfuss, M. Steigelmann, S. I. Khan, K. N.
Houk, Rationalization of Enantioselectivities in Dialkylzinc
Additions to Benzaldehyde Catalyzed by Fenchones
Derivatives. J. Org. Chem. 2000, 65, 77-82; (h) B. Goldfuss, M.
Steigelmann, Structure and Reactivity of Chiral Fenchone
Based Organozinc Catalysts. J. Mol. Model. 2000, 6, 166-170;
(i) B. Goldfuss, M. Steigelmann, F. Rominger, Increasing
Enantioselectivities and Reactivities by Stereochemical
Tuning: Fenchone-Based Catalysts in Dialkylzinc Additions to
Benzaldehyde. Eur. J. Org. Chem. 2000, 1785-1792; (j) M.
Steigelmann, Y. Nisar, F. Rominger, B. Goldfuss, Homo- and
Heterochiral Alkylzinc Fencholates: Linear on Nonlinear
Effects in Dialkylzinc Additions to Benzaldehyde. Chem. Eur.
J. 2002, 8, 5211-5218; (k) B. Goldfuss, M. Steigelmann, F.
Rominger, Chirale Modifizierung von n-Butyllithium:
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J. C. R. Thacker, P. L. A. Popelier, Fluorine Gauche Effect
Explained by Electrostatic Polarization Instead of
Hyperconjugation: An Interacting Quantum Atoms (IQA) and
Relative Energy Gradient (REG) Study. J. Phys. Chem. A 2018,
122, 1439-1450.
Steuerung
von
Stöchiometrie,
Struktur
und
Enantioselektivität durch modulare Fencholat-Einheiten.
Angew. Chem. 2000, 112, 4299-4302; Chirally Modified n-
Butyllithium: Tuning the Composition, Structure, and
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