Novel Chiral Ruthenium-Bis(Oxazolinyl)Pyridine and Bis-(Oxazolinyl)-Bipyridine Complexes: Asymmetric Cyclopropanation of Styrene with Diazoacetates

1995 ◽  
pp. 197-201
Author(s):  
Hisao Nishiyama ◽  
Hideki Matsumoto ◽  
Soon-Boon Park ◽  
Kenji Itoh
Keyword(s):  
Asymmetric Cyclopropanation

General Cyclopropane Assembly via Enantioselective Redox-Active Carbene Transfer to Aliphatic Olefins

2018 ◽  
Author(s):  
Marc Montesinos-Magraner ◽  
Matteo Costantini ◽  
Rodrigo Ramirez-Contreras ◽  
Michael E. Muratore ◽  
Magnus J. Johansson ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Chemical Space ◽  
Synthetic Approach ◽  
Asymmetric Cyclopropanation ◽  
Redox Active ◽  
Wide Range ◽  
Leaving Group ◽  
Stereoelectronic Properties ◽  
Carbene Transfer

Asymmetric cyclopropane synthesis currently requires bespoke strategies, methods, substrates and reagents, even when targeting similar compounds. This limits the speed and chemical space available for discovery campaigns. Here we introduce a practical and versatile diazocompound, and we demonstrate its performance in the first unified asymmetric synthesis of functionalized cyclopropanes. We found that the redox-active leaving group in this reagent enhances the reactivity and selectivity of geminal carbene transfer. This effect enabled the asymmetric cyclopropanation of a wide range of olefins including unactivated aliphatic alkenes, enabling the 3-step total synthesis of (–)-dictyopterene A. This unified synthetic approach delivers high enantioselectivities that are independent of the stereoelectronic properties of the functional groups transferred. Our results demonstrate that orthogonally-differentiated diazocompounds are viable and advantageous equivalents of single-carbon chirons<i>.</i>

Design and Characterization of Novel Dirhodium Coordination Polymers - The Impact of Ligand Size on Selectivity in Asymmetric Cyclopropanation

2021 ◽  
Author(s):  
Zhenzhong Li ◽  
Lorenz Roesler ◽  
Till Wissel ◽  
Hergen Breitzke ◽  
Kathrin Hofmann ◽  
...  
Keyword(s):  
Coordination Polymers ◽  
Ligand Exchange ◽  
Dicarboxylic Acids ◽  
Sem Images ◽  
Asymmetric Cyclopropanation ◽  
The Impact

Three chiral dirhodium coordination polymers Rh2-Ln (n=1-3) have been synthesized via ligand exchange between dirhodium trifluoroacetate Rh2(TFA)4 and differently sized chiral dicarboxylic acids derived from L-tert-leucine. SEM images indicate that...

Dearomatization of Electron-Deficient Nitrogen Heterocycles via Cobalt-Catalyzed Asymmetric Cyclopropanation

2016 ◽  
Vol 81 (8) ◽  
pp. 3070-3075 ◽  
Author(s):  
Amruta Joshi-Pangu ◽  
Ryan D. Cohen ◽  
Matthew T. Tudge ◽  
Yonggang Chen
Keyword(s):  
Nitrogen Heterocycles ◽  
Asymmetric Cyclopropanation

Asymmetric cyclopropanation of styrene with ethyl diazoacetate using a N 2 P 2 -ligand ruthenium(II) catalyst: axial ligand controlled enantioselectivity

2001 ◽  
Vol 42 (15) ◽  
pp. 2847-2849 ◽  
Author(s):  
Zhuo Zheng ◽  
Xiaoquan Yao ◽  
Chen Li ◽  
Huilin Chen ◽  
Xinquan Hu
Keyword(s):  
Axial Ligand ◽  
Ethyl Diazoacetate ◽  
Asymmetric Cyclopropanation

Pybox Monolithic Miniflow Reactors for Continuous Asymmetric Cyclopropanation Reaction under Conventional and Supercritical Conditions

2007 ◽  
Vol 72 (12) ◽  
pp. 4344-4350 ◽  
Author(s):  
M. I. Burguete ◽  
A. Cornejo ◽  
E. García-Verdugo ◽  
María J. Gil ◽  
S. V. Luis ◽  
...  
Keyword(s):  
Supercritical Conditions ◽  
Asymmetric Cyclopropanation

ChemInform Abstract: Asymmetric Cyclopropanation Reactions

ChemInform ◽  
2014 ◽  
Vol 45 (26) ◽  
pp. no-no
Author(s):  
Giuseppe Bartoli ◽  
Giorgio Bencivenni ◽  
Renato Dalpozzo
Keyword(s):  
Asymmetric Cyclopropanation

Sulfur‐Containing Chiral Bis(oxazolines) Tested in Copper‐Catalyzed Asymmetric Cyclopropanation

2005 ◽  
Vol 35 (20) ◽  
pp. 2665-2673 ◽  
Author(s):  
Ming Zhang Gao ◽  
Bo Wang ◽  
Deyuan Kong ◽  
Ralph A. Zingaro ◽  
Abraham Clearfield ◽  
...  
Keyword(s):  
Asymmetric Cyclopropanation ◽  
Sulfur Containing
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