ChemInform Abstract: Cyclic Tri- and Pentavalent Amidoesters and Diamides with a Stereogenic Phosphorus Atom in Asymmetric Synthesis. Part 1. Stoichiometric Reagents

ChemInform ◽  
2010 ◽  
Vol 41 (40) ◽  
pp. no-no
Author(s):  
Jozef Drabowicz ◽  
Dorota Krasowska ◽  
Andrzej Lopusinski ◽  
Thomas S. A. Heugebaert ◽  
Christian V. Stevens
Keyword(s):  
Asymmetric Synthesis ◽  
Phosphorus Atom

Asymmetric Synthesis of Organophosphorus Compounds using H-P reagents derived from Chiral Alcohols

2021 ◽  
Author(s):  
Tomasz K. Olszewski ◽  
Joseph Gbubele
Keyword(s):  
Asymmetric Synthesis ◽  
Phosphorus Atom ◽  
Organophosphorus Compounds ◽  
Chiral Alcohols

Chiral organophosphorus compounds, especially those containing C-stereogenic carbons in the proximity of the phosphorus atom, are known for their unique properties and have found wide applications that span from medicinal...

Cyclic tri- and Pentavalent Amidoesters and Diamides with a Stereogenic Phosphorus Atom in Asymmetric Synthesis: Part I: Stoichiometric Reagents

2010 ◽  
Vol 14 (5) ◽  
pp. 483-499 ◽  
Author(s):  
Jozef Drabowicz ◽  
Dorota Krasowska ◽  
Andrzej Lopusinski ◽  
Thomas Heugebaert ◽  
Christian Stevens
Keyword(s):  
Asymmetric Synthesis ◽  
Phosphorus Atom

Six-Membered Hetarenes with One Nitrogen or Phosphorus Atom

2005 ◽  
Author(s):  
D. StC. Black ◽  
D. Spitzner ◽  
P. A. Keller ◽  
R. D. Larsen ◽  
D. Cai ◽  
...  
Keyword(s):  
Phosphorus Atom

Potential Electron Scattering by Phosphorus Atom

2014 ◽  
Vol 59 (6) ◽  
pp. 569-580 ◽  
Author(s):  
V.I. Kelemen ◽  
◽  
M.M. Dovhanych ◽  
E.Yu. Remeta ◽  
◽  
...  
Keyword(s):  
Electron Scattering ◽  
Phosphorus Atom

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>

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