scholarly journals Asymmetric Synthesis of Spiropyrazolones by Sequential Organo- and Silver Catalysis

2015 ◽  
Vol 128 (5) ◽  
pp. 1829-1832 ◽  
Author(s):  
Daniel Hack ◽  
Alexander B. Dürr ◽  
Kristina Deckers ◽  
Pankaj Chauhan ◽  
Nico Seling ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Silver Catalysis

scholarly journals Asymmetric Synthesis of Spiropyrazolones by Sequential Organo- and Silver Catalysis

2015 ◽  
Vol 55 (5) ◽  
pp. 1797-1800 ◽  
Author(s):  
Daniel Hack ◽  
Alexander B. Dürr ◽  
Kristina Deckers ◽  
Pankaj Chauhan ◽  
Nico Seling ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Silver Catalysis

ChemInform Abstract: Asymmetric Synthesis of Spiropyrazolones by Sequential Organo- and Silver Catalysis.

ChemInform ◽  
2016 ◽  
Vol 47 (22) ◽  
Author(s):  
Daniel Hack ◽  
Alexander B. Duerr ◽  
Kristina Deckers ◽  
Pankaj Chauhan ◽  
Nico Seling ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Silver Catalysis

scholarly journals Asymmetric Synthesis of Tetrahydrobenzofurans and Annulated Dihydropyrans via Cooperative One-Pot Organo- and Silver-Catalysis

Synthesis ◽  
2016 ◽  
Vol 48 (19) ◽  
pp. 3207-3216 ◽  
Author(s):  
Uğur Kaya ◽  
Pankaj Chauhan ◽  
Kristina Deckers ◽  
Rakesh Puttreddy ◽  
Kari Rissanen ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Addition ◽  
Catalyst Loading ◽  
One Pot ◽  
Silver Catalysis ◽  
Asymmetric Michael Addition ◽  
Low Catalyst Loading

A low catalyst loading of a squaramide (0.5 mol%) and a silver(I) salt (1 mol%) efficiently catalyzes a one-pot asymmetric Michael addition/hydroalkoxylation reaction between 1,3-diketones and alkyne-tethered nitroalkenes. Depending on the 1,3-dicarbonyl substrate this cooperative catalytic approach opens access to tetrahydrobenzofurans or annulated dihydropyrans in moderate to excellent yields and very good to excellent enantioselectivities.

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>

Sign in / Sign up

Export Citation Format

Share Document