Access the full text.
Sign up today, get DeepDyve free for 14 days.
Loading next page...
/lp/wiley/catalytic-enantioselective-alkynylation-of-trifluoromethyl-ketones-cFKdMFKA7u
References (54)
-
Li Lin, Rui Wang (2009)
Recent Advance in Asymmetric Alkynylation of KetonesChemInform, 41
-
S. Bartsch, R. Kourist, U. Bornscheuer (2008)
Complete inversion of enantioselectivity towards acetylated tertiary alcohols by a double mutant of a Bacillus subtilis esterase.Angewandte Chemie, 47 8
-
K. Aikawa, Y. Hioki, K. Mikami (2010)
Highly enantioselective alkynylation of trifluoropyruvate with alkynylsilanes catalyzed by the BINAP-Pd complex: access to α-trifluoromethyl-substituted tertiary alcohols.Organic letters, 12 24
-
Kuo-Hui Wu, H. Gau (2004)
Mechanism of Asymmetric Dialkylzinc Addition to Aldehydes Catalyzed by Titanium(IV) Complexes of N-Sulfonylated β-Amino AlcoholsOrganometallics, 23
-
J. Nie, Hong-Chao Guo, D. Cahard, Jun‐An Ma (2011)
Asymmetric construction of stereogenic carbon centers featuring a trifluoromethyl group from prochiral trifluoromethylated substrates.Chemical reviews, 111 2
-
P. Cozzi, Robert Hilgraf, N. Zimmermann (2004)
Acetylenes in Catalysis: Enantioselective Additions to Carbonyl Groups and Imines and Applications BeyondEuropean Journal of Organic Chemistry, 2004
-
Jochen and, E. Carreira (1998)
Apparent Catalytic Generation of Chiral Metal Enolates: Enantioselective Dienolate Additions to Aldehydes Mediated by Tol-BINAP·Cu(II) Fluoride ComplexesJournal of the American Chemical Society, 120
-
B. Heinze, R. Kourist, Linda Fransson, K. Hult, U. Bornscheuer (2007)
Highly enantioselective kinetic resolution of two tertiary alcohols using mutants of an esterase from Bacillus subtilis.Protein engineering, design & selection : PEDS, 20 3
-
Li Lin, Xianxing Jiang, Weixia Liu, L. Qiu, Zhaoqing Xu, Jiangke Xu, A. Chan, Rui Wang (2007)
Highly enantioselective synthesis of gamma-hydroxy-alpha,beta-acetylenic esters catalyzed by a beta-sulfonamide alcohol.Organic letters, 9 12
-
D. Moore, L. Pu (2002)
BINOL-catalyzed highly enantioselective terminal alkyne additions to aromatic aldehydes.Organic letters, 4 11
-
(2010)
During the revision of this manuscript, a palladium-catalyzed enantioselective alkynylation of trifluoropyruvate was described -
Diego Ramón, M. Yus (2004)
Chirale tertiäre Alkohole durch katalytische enantioselektive Addition von unreaktiven Zinkreagentien an schwach elektrophile KetoneAngewandte Chemie, 116
-
K. Kirk (2008)
Fluorination in Medicinal Chemistry: Methods, Strategies, and Recent DevelopmentsOrganic Process Research & Development, 12
-
D. Ramón, M. Yus (2004)
Chiral tertiary alcohols made by catalytic enantioselective addition of unreactive zinc reagents to poorly electrophilic ketones?Angewandte Chemie, 43 3
-
(2004)
For recent examples of titanium complexes as catalysts in asymmetric alkynylation -
(2004)
Highly enantioselective alkyne additions to aldehydes in the presence of 1,1'-bi-2-naphthol and hexamethylphosphoramide.Proceedings of the National Academy of Sciences of the United States of America, 101 15
-
R. Chambers (1973)
Fluorine in organic chemistry -
The B3LYP calculations were carried out according to Ahlrichss SVP all electron basis set model using pseudo-potential basis sets (LAN2 MB) for Ba, Zn, Ti, and 6-31G(d) basis set for -
L. Tan, Cheng-yi Chen, R. Tillyer, E. Grabowski, P. Reider (1999)
A Novel, Highly Enantioselective Ketone Alkynylation Reaction Mediated by Chiral Zinc Aminoalkoxides.Angewandte Chemie, 38 5
-
Keith Fagnou, Mark Lautens (2002)
Der Einfluss von Halogenidionen in der ÜbergangsmetallkatalyseAngewandte Chemie, 114
-
G. Lu, Yue‐Ming Li, Xingshu Li, A. Chan (2005)
Synthesis and application of new chiral catalysts for asymmetric alkynylation reactionsCoordination Chemistry Reviews, 249
-
Hydride and fluoride are classified as hard ligands in coordination chemistry. In addition, the Van der Waals radius of fluorine of 1 -
Jun‐An Ma, D. Cahard (2008)
Update 1 of: Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions.Chemical reviews, 108 9
-
A. Thompson, E. Corley, Martha Huntington, E. Grabowski (1995)
Use of an ephedrine alkoxide to mediate enantioselective addition of an acetylide to a prochiral ketone: asymmetric synthesis of the reverse transcriptase inhibitor L-743,726Tetrahedron Letters, 36
-
X. Verdaguer, Udo Lange, Matthew Reding, S. Buchwald (1996)
Highly Enantioselective Imine Hydrosilylation Using (S,S)-Ethylenebis(η5-tetrahydroindenyl)titanium DifluorideJournal of the American Chemical Society, 118
-
B. Pagenkopf, E. Carreira (1999)
Transition Metal Fluoride Complexes in Asymmetric CatalysisChemistry: A European Journal, 5
-
K. Fagnou, M. Lautens (2002)
Halide effects in transition metal catalysis.Angewandte Chemie, 41 1
-
Sebastian Bartsch, Robert Kourist, U. Bornscheuer (2008)
Vollständige Umkehrung der Enantioselektivität gegen acetylierte tertiäre Alkohole durch eine Doppelmutation in einer Esterase aus Bacillus subtilisAngewandte Chemie, 120
-
Romano Dorta, P. Egli, A. Zürcher, A. Togni (1997)
The [IrCl(Diphosphine)]2/Fluoride System. Developing Catalytic Asymmetric Olefin HydroaminationJournal of the American Chemical Society, 119
-
(2004)
Special Issue on “Fluorine in the Life Sciences -
K. Müller, Christoph Faeh, F. Diederich (2007)
Fluorine in Pharmaceuticals: Looking Beyond IntuitionScience, 317
-
B. Trost, A. Weiss (2009)
The Enantioselective Addition of Alkyne Nucleophiles to Carbonyl Groups.Advanced synthesis & catalysis, 351 7-8
-
D. Engel, G. Dudley (2009)
The Meyer-Schuster rearrangement for the synthesis of alpha,beta-unsaturated carbonyl compounds.Organic & biomolecular chemistry, 7 20
-
Donald Gauthier, Erick Carreira (1996)
Katalytische, enantioselektive Addition von Allylsilanen an Aldehyde: Bildung eines neuartigen reaktiven TiIV‐Komplexes aus TiF4Angewandte Chemie, 108
-
B. Jiang, Yanshu Feng (2002)
Enantioselective alkynylation of a prochiral ketone catalyzed by C2-symmetric diamino diolsTetrahedron Letters, 43
-
G. Lu, Xingshu Li, W. Chan, A. Chan (2002)
Titanium-catalyzed enantioselective alkynylation of aldehydes.Chemical communications, 2
-
The enantioselective alkynylation of 2'-chloro-2,2,2-trifluoroaceto-phenone with phenylacetylene -
L. Lavanant, L. Toupet, C. Lehmann, J. Carpentier (2005)
Group 4 metal complexes of nitrogen-bridged dialkoxide ligands : Synthesis, structure, and polymerization activity studiesOrganometallics, 24
-
Lushi Tan, Cheng-yi Chen, Richard Tillyer, Edward Grabowski, Paul Reider (1999)
Eine neue, hochenantioselektive Alkinylierung von Ketonen, die durch chirale Zinkaminoalkoxide gesteuert wirdAngewandte Chemie, 111
-
G. Gao, D. Moore, R. Xie, L. Pu (2002)
Highly enantioselective phenylacetylene additions to both aliphatic and aromatic aldehydes.Organic letters, 4 23
-
G. Hembury, V. Borovkov, Y. Inoue (2008)
Chirality-sensing supramolecular systems.Chemical reviews, 108 1
-
B. Pagenkopf, E. Carreira (1998)
Titanium fluoride complexes as catalysts for the enantioselective addition of Me3Al to aldehydesTetrahedron Letters, 39
-
L. Pu (2003)
Asymmetric Alkynylzinc Additions to Aldehydes and KetonesChemInform, 35
-
(2007)
For biocatalytic kinetic resolution of racemic substrates for the preparation of chiral trifluoromethylated propargylic tertiary alcohols, see: a) -
Joanna Day, R. Baghurst, Robert Strevens, M. Light, M. Hursthouse, B. Stengel, I. Fallis, S. Aldridge (2007)
Influence of ligand backbone flexibility in group 4 metal complexes of tetradentate mixed tertiary amine/alkoxide ligandsNew Journal of Chemistry, 31
-
Natalie Ljungdahl, Nina Kann (2009)
Übergangsmetallkatalysierte propargylische SubstitutionenAngewandte Chemie, 121
-
Natalie Ljungdahl, N. Kann (2009)
Transition-metal-catalyzed propargylic substitution.Angewandte Chemie, 48 4
-
A. Thompson, E. Corley, Martha Huntington, E. Grabowski, and Remenar, D. Collum (1998)
Lithium Ephedrate-Mediated Addition of a Lithium Acetylide to a Ketone: Solution Structures and Relative Reactivities of Mixed Aggregates Underlying the High EnantioselectivitiesJournal of the American Chemical Society, 120
-
(2011)
Catalytic enantioselective alkynylation of trifluoromethyl ketones: pronounced metal fluoride effects and implications of zinc-to-titanium transmetallation. -
D. Gauthier, E. Carreira (1996)
Catalytic, Enantioselective Addition of Allylsilanes to Aldehydes: Generation of a Novel, Reactive TiIV Complex from TiF4Angewandte Chemie, 35
-
Feng Xu, R. Reamer, R. Tillyer, Jordan Cummins, E. Grabowski, P. Reider, D. Collum, J. Huffman (2000)
Highly Enantioselective 1,2-Addition of Lithium Acetylide-Ephedrate Complexes: Spectroscopic Evidence for Reaction Proceeding via a 2:2 Tetramer, and X-ray Characterization of Related ComplexesJournal of the American Chemical Society, 122
-
R. Motoki, M. Kanai, M. Shibasaki (2007)
Copper(I) alkoxide-catalyzed alkynylation of trifluoromethyl ketones.Organic letters, 9 16
-
(1995)
For selected reviews, see: a) Modern Acetylene Chemistry -
S. Hsieh, H. Gau (2006)
Enantioselective addition of diethylzinc to aldehydes catalyzed by titanium(IV) complexes of N-sulfonylated beta-amino alcohols with four stereogenic centers.Chirality, 18 8
- Publisher
- Wiley
- Copyright
- Copyright © 2011 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
- ISSN
- 1433-7851
- eISSN
- 1521-3773
- DOI
- 10.1002/anie.201007341
- pmid
- 21452368
- Publisher site
- See Article on Publisher Site
Abstract
Lost in transmetalation: The titanium(IV)‐catalyzed title reaction, utilizing chiral cinchona alkaloids as ligands (L1 and L2), was developed for the synthesis of both enantiomers of trifluoromethylated propargylic tertiary alcohols in high yield and enantioselectivity. Small amounts of BaF2 were found to be essential for maintaining high levels of reactivity and enantioselectivity.
Journal
Angewandte Chemie International Edition – Wiley
Published: Apr 4, 2011