2 publications

2 publications

DNA‐Based Asymmetric Inverse Electron‐Demand Hetero‐Diels–Alder

Arseniyadis, S.; Campagne, J.; Smietana, M.

Chem. Eur. J. 2020, 26, 3519-3523, 10.1002/chem.202000516

While artificial cyclases hold great promise in chemical synthesis, this work presents the first example of a DNA-catalyzed inverse electron-demand hetero-Diels–Alder (IEDHDA) between dihydrofuran and various α,β-unsaturated acyl imidazoles. The resulting fused bicyclic O,O-acetals containing three contiguous stereogenic centers are obtained in high yields (up to 99 %) and excellent diastereo- (up to >99:1 dr) and enantioselectivities (up to 95 % ee) using a low catalyst loading. Most importantly, these results show that the concept of DNA-based asymmetric catalysis can be expanded to new synthetic transformations offering an efficient, sustainable, and highly selective tool for the construction of chiral building blocks.


Metal: Cu
Ligand type: Cu(dmbipy)(NO3)2
Host protein: DNA
Anchoring strategy: Supramolecular
Optimization: Chemical
Max TON: 3.33
ee: 95
PDB: ---
Notes: ---

Polymerization of Phenylacetylene by Rhodium Complexes within a Discrete Space of apo-Ferritin

Ueno, T.; Watanabe, Y.

J. Am. Chem. Soc. 2009, 131, 6958-6960, 10.1021/ja901234j

Polymerization reactions of phenylacetylene derivatives are promoted by rhodium complexes within the discrete space of apo-ferritin in aqueous media. The catalytic reaction provides polymers with restricted molecular weight and a narrow molecular weight distribution. These results suggest that protein nanocages have potential for use as various reaction spaces through immobilization of metal catalysts on the interior surfaces of the protein cages.


Metal: Rh
Ligand type: Norbornadiene
Host protein: Ferritin
Anchoring strategy: Dative
Optimization: ---
Max TON: ---
ee: ---
PDB: 2ZUR
Notes: ---