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Design of Axially Chiral Dicarboxylic Acid for Asymmetric Mannich Reaction of Arylaldehyde N-Boc Imines and Diazo Compounds
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Abstract
An axially chiral dicarboxylic acid has been prepared as a new class of chiral hydrogen-bonding catalysts and applied to the highly enantioselective Mannich reaction of arylaldehyde N-Boc imines and diazo compounds.
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This article has been cited by 22 ACS Journal articles (5 most recent appear below).
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Norie Momiyama, Tohru Konno, Yuichi Furiya, Takeaki Iwamoto, and Masahiro TeradaJournal of the American Chemical Society2011 133 (48), 19294-19297Chiral bis-phosphoric acid 1 was designed to identify a new class of structural features in chiral Brønsted acid catalysts. X-ray diffraction analysis revealed the single atropisomer 1, bearing S axial chirality at 3,3′-biaryl substituents on (R)-...
D2-Symmetric Dirhodium Catalyst Derived from a 1,2,2-Triarylcyclopropanecarboxylate Ligand: Design, Synthesis and Application
Changming Qin, Vyacheslav Boyarskikh, Jørn H. Hansen, Kenneth I. Hardcastle, Djamaladdin G. Musaev, and Huw M. L. DaviesJournal of the American Chemical Society2011 133 (47), 19198-19204D2-Symmetric Dirhodium Catalyst Derived from a 1,2,2-Triarylcyclopropanecarboxylate Ligand: Design, Synthesis and Application
Changming Qin, Vyacheslav Boyarskikh, Jørn H. Hansen, Kenneth I. Hardcastle, Djamaladdin G. Musaev, and Huw M. L. DaviesJournal of the American Chemical Society2011 133 (47), 19198-19204Dirhodium tetrakis-(R)-(1-(4-bromophenyl)-2,2-diphenylcyclopropanecarboxylate) (Rh2(R-BTPCP)4) was found to be an effective chiral catalyst for enantioselective reactions of aryl- and styryldiazoacetates. Highly enantioselective cyclopropanations, tandem ...
Asymmetric Catalytic Cycloetherification Mediated by Bifunctional Organocatalysts
Keisuke Asano and Seijiro MatsubaraJournal of the American Chemical Society2011 133 (42), 16711-16713Asymmetric Catalytic Cycloetherification Mediated by Bifunctional Organocatalysts
Keisuke Asano and Seijiro MatsubaraJournal of the American Chemical Society2011 133 (42), 16711-16713Oxacyclic structures such as tetrahydrofuran (THF) rings are commonly found in many bioactive compounds, and this has led to several efforts toward their stereoselective syntheses. However, the process of catalytic asymmetric cycloetherification for their ...
Humidity-Driven Reversible Transformation and Guest Inclusion in a Two-Dimensional Coordination Framework Tailored by Organic Polyamine Cation
Robert Podgajny, Szymon Choraży, Wojciech Nitek, Andrzej Budziak, Michał Rams, Carlos J. Gómez-García, Marcin Oszajca, Wiesław Łasocha, and Barbara SiekluckaCrystal Growth & Design2011 11 (9), 3866-3876Humidity-Driven Reversible Transformation and Guest Inclusion in a Two-Dimensional Coordination Framework Tailored by Organic Polyamine Cation
Robert Podgajny, Szymon Choraży, Wojciech Nitek, Andrzej Budziak, Michał Rams, Carlos J. Gómez-García, Marcin Oszajca, Wiesław Łasocha, and Barbara SiekluckaCrystal Growth & Design2011 11 (9), 3866-3876Using a polyamine cation tetrenH55+ (tetren = tetraethylenepentaamine), we tailored the dynamic layered material (tetrenH5)1.6{CoII(H2O)2[MIV(CN)8]}4·xH2O (1, M = W, x = 12; 2, M = Mo, x = 11.2). 1 and 2 consist of strongly corrugated two-dimensional (2D) ...
Synthetic Application and Structural Elucidation of Axially Chiral Dicarboxylic Acid: Asymmetric Mannich-type Reaction with Diazoacetate, (Diazomethyl)phosphonate, and (Diazomethyl)sulfone
Takuya Hashimoto, Hidenori Kimura, Hiroki Nakatsu, and Keiji MaruokaThe Journal of Organic Chemistry2011 76 (15), 6030-6037Synthetic Application and Structural Elucidation of Axially Chiral Dicarboxylic Acid: Asymmetric Mannich-type Reaction with Diazoacetate, (Diazomethyl)phosphonate, and (Diazomethyl)sulfone
Takuya Hashimoto, Hidenori Kimura, Hiroki Nakatsu, and Keiji MaruokaThe Journal of Organic Chemistry2011 76 (15), 6030-6037The past decade has witnessed the burgeoning research fields of chiral Brønsted acid catalysis. However, carboxylic acids, arguably the most general acids in organic chemistry, have rarely been used as chiral Brønsted acid catalysts. In this context, we ...
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History
- Published In Issue August 22, 2007
- Received February 26, 2007
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