Di-Palladium Complexes are Active Catalysts for Mono-N-Protected Amino Acid-Accelerated Enantioselective C–H Functionalization

ACS Catalysis ◽  
2019 ◽  
Vol 9 (12) ◽  
pp. 11386-11397 ◽  
Author(s):  
Joseph J. Gair ◽  
Brandon E. Haines ◽  
Alexander S. Filatov ◽  
Djamaladdin G. Musaev ◽  
Jared C. Lewis
Keyword(s):  
Amino Acid ◽  
Palladium Complexes ◽  
Protected Amino Acid

Di-Palladium Complexes are Active Catalysts for Mono-N-Protected Amino Acid Accelerated Enantioselective C-H Functionalization

2019 ◽  
Author(s):  
Joseph Gair ◽  
Brandon E. Haines ◽  
Alexander S. Filatov ◽  
Djamaladdin G. Musaev ◽  
Jared C. Lewis
Keyword(s):  
Amino Acid ◽  
Density Functional ◽  
Kinetic Method ◽  
Experimental Studies ◽  
Density Functional Theory Calculations ◽  
Palladium Complexes ◽  
X Ray Diffraction ◽  
Protected Amino Acid ◽  
Palladium Catalyzed ◽  
Method Of Continuous Variation

The role of mono-protected amino acid (MPAA) ligands in accelerating enantioselective cyclopalladation and palladium catalyzed C-H func-tionalization was investigated using kinetic, spectroscopic, and computational methods. Single crystal X-ray diffraction and NMR spectroscopy demonstrate that MPAA ligands bind catalytically competent di-palladium complexes as bridging carboxylates. The catalytic relevance of the observed di-palladium species was evaluated by kinetic analysis. The kinetic method of continuous variation demonstrated that a complex contain-ing a single MPAA-bridged di-palladium core (Pd2(MPAA)1) is an active catalyst for the reactions studied. The experimental studies are con-sistent with density functional theory calculations that indicate enantioinduction can be achieved by a single MPAA ligand bridging a di-palladium catalyst through secondary sphere hydrogen-bonding interactions that lower the barrier to C-H activation of the major enantiomer.<br>

Di-Palladium Complexes are Active Catalysts for Mono-N-Protected Amino Acid Accelerated Enantioselective C-H Functionalization

2019 ◽  
Author(s):  
Joseph Gair ◽  
Brandon E. Haines ◽  
Alexander S. Filatov ◽  
Djamaladdin G. Musaev ◽  
Jared C. Lewis
Keyword(s):  
Amino Acid ◽  
Density Functional ◽  
Kinetic Method ◽  
Experimental Studies ◽  
Density Functional Theory Calculations ◽  
Palladium Complexes ◽  
X Ray Diffraction ◽  
Protected Amino Acid ◽  
Palladium Catalyzed ◽  
Method Of Continuous Variation

The role of mono-protected amino acid (MPAA) ligands in accelerating enantioselective cyclopalladation and palladium catalyzed C-H func-tionalization was investigated using kinetic, spectroscopic, and computational methods. Single crystal X-ray diffraction and NMR spectroscopy demonstrate that MPAA ligands bind catalytically competent di-palladium complexes as bridging carboxylates. The catalytic relevance of the observed di-palladium species was evaluated by kinetic analysis. The kinetic method of continuous variation demonstrated that a complex contain-ing a single MPAA-bridged di-palladium core (Pd2(MPAA)1) is an active catalyst for the reactions studied. The experimental studies are con-sistent with density functional theory calculations that indicate enantioinduction can be achieved by a single MPAA ligand bridging a di-palladium catalyst through secondary sphere hydrogen-bonding interactions that lower the barrier to C-H activation of the major enantiomer.<br>

Di-Palladium Complexes are Active Catalysts for Mono-N-Protected Amino Acid Accelerated Enantioselective C-H Functionalization

2019 ◽  
Author(s):  
Joseph Gair ◽  
Brandon E. Haines ◽  
Alexander S. Filatov ◽  
Djamaladdin G. Musaev ◽  
Jared C. Lewis
Keyword(s):  
Amino Acid ◽  
Density Functional ◽  
Kinetic Method ◽  
Experimental Studies ◽  
Density Functional Theory Calculations ◽  
Palladium Complexes ◽  
X Ray Diffraction ◽  
Protected Amino Acid ◽  
Palladium Catalyzed ◽  
Method Of Continuous Variation

The role of mono-protected amino acid (MPAA) ligands in accelerating enantioselective cyclopalladation and palladium catalyzed C-H func-tionalization was investigated using kinetic, spectroscopic, and computational methods. Single crystal X-ray diffraction and NMR spectroscopy demonstrate that MPAA ligands bind catalytically competent di-palladium complexes as bridging carboxylates. The catalytic relevance of the observed di-palladium species was evaluated by kinetic analysis. The kinetic method of continuous variation demonstrated that a complex contain-ing a single MPAA-bridged di-palladium core (Pd2(MPAA)1) is an active catalyst for the reactions studied. The experimental studies are con-sistent with density functional theory calculations that indicate enantioinduction can be achieved by a single MPAA ligand bridging a di-palladium catalyst through secondary sphere hydrogen-bonding interactions that lower the barrier to C-H activation of the major enantiomer.<br>

A facile one pot route for the synthesis of imide tethered peptidomimetics

2016 ◽  
Vol 14 (2) ◽  
pp. 556-563 ◽  
Author(s):  
Veladi Panduranga ◽  
Girish Prabhu ◽  
Roopesh Kumar ◽  
Basavaprabhu Basavaprabhu ◽  
Vommina V. Sureshbabu
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Efficient Method ◽  
One Pot ◽  
Protected Amino Acid

A simple and efficient method for the synthesis of N,N’-orthogonally protected imide tethered peptidomimetics is presented. The imide peptidomimetics were synthesized by coupling the in situ generated selenocarboxylate of Nα-protected amino acids with Nα-protected amino acid azides in good yields.

ChemInform Abstract: Urethane-Protected Amino Acid N-Carboxy Anhydrides and Their Use in Peptide Synthesis.

ChemInform ◽  
2010 ◽  
Vol 22 (2) ◽  
pp. no-no
Author(s):  
W. D. FULLER ◽  
M. P. COHEN ◽  
M. SHABANKAREH ◽  
R. K. BLAIR ◽  
M. GOODMAN ◽  
...  
Keyword(s):  
Amino Acid ◽  
Peptide Synthesis ◽  
Protected Amino Acid

Dynamic Kinetic Resolution of N-Protected Amino Acid Esters via Phase-Transfer Catalytic Base Hydrolysis

ACS Catalysis ◽  
2018 ◽  
Vol 8 (7) ◽  
pp. 5708-5713 ◽  
Author(s):  
Eiji Yamamoto ◽  
Kodai Wakafuji ◽  
Yuho Furutachi ◽  
Kaoru Kobayashi ◽  
Takashi Kamachi ◽  
...  
Keyword(s):  
Amino Acid ◽  
Kinetic Resolution ◽  
Phase Transfer ◽  
Base Hydrolysis ◽  
Amino Acid Esters ◽  
Dynamic Kinetic Resolution ◽  
Protected Amino Acid ◽  
Acid Esters
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