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New Journal of Chemistry
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ARTICLE
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Chem. 2012, 449-462; for other synthesis of chiral 2-
methylchromones see: (e) A. V. R. Rao, A. S. Gaitonde, K. R.
C. Prakash and S. P. Rao, A concise synthesis of chiral 2-
methyl chroman-4-ones: Stereo selective build-up the
chromanol moiety of anti-HIV agent calanolide A.
Tetrahedron Lett. 1994, 35, 6347-6350; (f) Y. Noda and M.
Watanabe, Synthesis of Both Enantiomers of Flavanone and
2-Methylchromanone. Helv. Chim. Acta. 2002, 85, 3473-
3477; (g) Z. Zhang, C. Pan, Z. Wang, Synthesis of
Aromaten. Bequemer Zugang zuDO2I:,120‘.-1d0i3s9u/bCs8tNitJu0i5e8r8te6nE
Biphenylderivaten. J. Organomet. Chem. 1982, 228, 107-118;
(c) 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; (d) B. Goldfuss, M. Steigelmann,
Structure and Reactivity of Chiral Fenchone Based
Organozinc Catalysts. J. Mol. Model. 2000, 6, 166-170; (e) 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; (f) 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.
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chromanones:
a novel palladium-catalyzed Wacker-type
oxidative cyclization involving 1,5-hydride alkyl to palladium
migration. Chem. Commun. 2007, 0, 4686-4688.
(a) G. P. Ellis, Chromenes, Chromanones and Chromones,
John Wiley & Sons, New York, 1977; (b) B. A. Bohm and J. B.
Harbone, The Flavonoids. Advances in Research Since 1980,
ed. B. A. Bohm and J. B. Harbone, Chapman and Hall, New
York, 1988; (c) B. A. Bohm, Introduction to Flavonoids,
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Harwood Academic Publishers, Amsterdam, 1998; (d) Ø. M. 10 (a) B. Goldfuss, M. Steigelmann, F. Rominger, Chirale
Andersen and K. R. Markham, Flavonoids: Chemistry,
Biochemistry and Applications, CRC, Taylor & Francis, Boca
Raton, FL, 2006.
For synthesis of BINOL see: (a) J. Brussee, A. C. A. Jansen, A
highly stereoselective synthesis of s(-)-[1,1’-binaphthalene]-
2,2’-diol. Tetrahedron Lett. 1983, 24, 3261-3262; (b) M. Noji,
M. Nakajima, K. Koga, A New Catalytic System for Aerobic
Oxidative Coupling of 2-Naphthol Derivatives by the Use of
CuCl-Amine Complex: A Practical Synthesis of Binaphthol
Derivatives. Tetrahedron Lett. 1994, 35, 7983-7984.
For synthesis of TADDOL see: (a) Seebach, A. K. Beck, R.
Imwinkelzied, S. Roggo, A. Wonnacott, Chirale
Alkoxytitan(IV)-Komplexe für enantioselektive nucleophile
Additionen an Aldehyde und als Lewis-Säuren in Diels-Alder-
Reaktionen. Helv. Chim. Acta 1987, 70, 954-974; for chiral
phosphites see: (b) A. Alexakis, J. Burton, J. Vastra, C.
Benhaim, X. Fournioux, A. van den Heuvel, J.-M. Levêque, F.
Mazé, S. Rosset, Synthesis and Application of Chiral
Phosphorus Ligands Derived from TADDOL for the
Asymmetric Conjugate Addition of Diethyl Zinc to Enones.
Eur. J. Org. Chem. 2000, 4011-4027.
Modifizierung von n-Butyllithium: 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 Enantioselectivity with Modular
Fencholates. Angew. Chem. Int. Ed. 2000, 39, 4133-4136; (b)
B. Goldfuss, M. Steigelmann, F. Rominger, H. Urtel, Chiral
Modular n-Butyllithium Aggregates: nBuLi Complexes with
Anisyl Fencholates. Chem. Eur. J. 2001, 7, 4456-4464; (c) B.
Goldfuss, Organolithiums in Enantioselective Additions to n*
and σ* Carbon-Oxygen Electrophiles. Synthesis 2005, 2271-
2280; (d) B. Goldfuss, M. Steigelmann, T. Löschmann, G.
Schilling, F. Rominger, Chem. Eur. J. 2005, 11, 4019-4023; (e)
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; (f) M. Leven, D. Müller,
B. Goldfuss, Enantioselective Alkynylation of Aromatic
Aldehydes: Pyridyl Phenylene Terpeneol Catalysts with
Flexible Biaryl Axes. Synlett 2011, 2505-2508; (g) 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.
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(a) B. Goldfuss, F. Rominger, The Origin of Atropisomerism in
2,2’-Bis((1R,2R,4S)-2-hydroxy-1,3,3-
trimethylbicyclo[2.2.1]hept-2-yl)-1,1’-biphenyl:
Synthesis,
Structure and Energetics. Tetrahedron 2000, 56, 881-884; (b) 11 R. Blanco-Trillo, M. Leven, J.-M. Neudörfl, B. Goldfuss,
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?
Electronegativity Governs Enantioselectivity: Alkyl-Aryl
Cross-Coupling with Fenchol-Based Palladium-Phosphorus
Halide Catalysts. Adv. Synth. Catal. 2012, 354, 1451-1465.
12 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. Beilstein J. Org. Chem. 2006, 2, 7.
Phosphorus Derivatives of Fenchol. Chem. Eur. J. 2001, 7, 13 T. Kop-Weiershausen, J. Lex, J.-M. Neudörfl, B. Goldfuss, An
2028-2033; (d) B. Goldfuss, T. Löschmann, F. Rominger,
Ligand Bite Governs Enantioselectivity: Electronic and Steric
Control in Pd-Catalyzed Allylic Alkylations by Modular
Fenchyl Phosphinites (FENOPs). Chem. Eur. J. 2004, 10, 5422-
5427; (e) F. Soki, J.-M. Neudörfl, B. Goldfuss, Surprising
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; as far as we know the first application
of a hydrido phoshpite ligand in Cu-catalyzed 1,4-addition.
fenchone induced cyclization: synthesis of the new chiral diol 14 (a) K. Endo, M. Ogawa, T. Shibata, Multinuclear Catalyst for
biphenyl-2,2’-sulfone-3,3’-bisfenchol (BISFOL). Tetrahedron
2005, 61, 10449-10453; (f) 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.
Copper-Catalyzed Asymmetric Conjugate Addition of
Organozinc Reagents. Angew. Chem. Int. Ed. 2010, 49, 2410-
2413; (b) Q. Jiang, T. Guo, Q. Wang, P. Wu, Z. Yu, Rhodium(I)-
Catalyzed Arylation of β-Chloro Ketones and Related
Derivatives through Domino Dehydrochlorination/ Conjugate
Addition. Adv. Synth. Catal. 2013, 355, 1874-1880; (c) T.
Yang, Y. Zhang, P. Cao, M. Wang, L. Li, D. Li, J. Liao, Copper-
catalyzed enantioselective conjugate addition of diethylzinc
to acyclic enones with chiral sulfoxide-phosphine ligands.
Tetrahedron 2016, 72, 2707-2711; (d) K. Endo, D. Hamada, S.
Yakeishi, T. Shibata, Effect of Multinuclear Copper/Aluminum
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(a) 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-
trimethylbicyclo[2.2.1]heptanes.
methoxyphenyl)-1,3,3-
Organometallics 1999, 18, 2927-2929; (b) W. Neugebauer, A.
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