Daniel Seidel

Catalytic enantioselective additions of indoles to nitroalkenes.

A new design principle that provides access to more active thiourea catalysts is described. Highly enantioselective additions of indoles to nitroalkenes are reported using a new quinolinium thioamide catalyst.

Merging Nucleophilic and Hydrogen Bonding Catalysis: An Anion Binding Approach to the Kinetic Resolution of Amines

A new concept for asymmetric nucleophilic catalysis is presented. Acyl pyridinium salts derived from 4-(dimethylamino)pyridine (DMAP) and benzoic anhydride are rendered chiral via interaction with a chiral thiourea anion receptor. The power of this concept is demonstrated in the context of kinetic amine resolution.

Catalytic Enantioselective Intramolecular Redox Reactions: Ring-Fused Tetrahydroquinolines

The first example of a catalytic enantioselective intramolecular hydride shift/ring closure reaction is reported. This redox neutral reaction cascade allows for the efficient formation of ring-fused tetrahydroquinolines in high enantioselectivities.

Nontraditional Reactions of Azomethine Ylides: Decarboxylative Three-Component Couplings of α-Amino Acids

New reactions of azomethine ylides with nontraditional dipolarophiles are reported. Azomethine ylides, formed in situ via decarboxylative condensations of alpha-amino acids with aldehydes, undergo reactions with naphthols, indoles, alkynes, and nitroalkanes.

Lewis Acid Catalyzed Formation of Tetrahydroquinolines via an Intramolecular Redox Process

Polycyclic tetrahydroquinolines were prepared by an efficient Lewis acid catalyzed 1,5-hydride shift, ring closure sequence. Gadolinium triflate was identified as a catalyst that is superior to scandium triflate as well as other Lewis acids. An approach toward a catalytic enantioselective variant is also described.

CH Bond Functionalization through Intramolecular Hydride Transfer

Known for over a century, reactions that involve intramolecular hydride-transfer events have experienced a recent resurgence. Undoubtedly responsible for the increased interest in this research area is the realization that hydride shifts represent an attractive avenue for C-H bond functionalization. The redox-neutral nature of these complexity-enhancing transformations makes them ideal for sustainable reaction development. This Review summarizes recent progress in this field while highlighting key historical contributions.

Facile Formation of Cyclic Aminals through a Brønsted Acid-Promoted Redox Process

Cyclic aminals were prepared through a Brønsted acid-promoted reaction. This redox neutral process involves iminium ion formation, 1,5 H-transfer, followed by ring closure.

Redox-Neutral Indole Annulation Cascades

Aminobenzaldehydes react with indoles in an unprecedented cascade reaction. This acid-catalyzed redox-neutral annulation proceeds via a condensation/1,5-hydride shift/ring-closure sequence. Polycyclic azepinoindoles and related compounds are obtained in a single step with good to excellent yields.

Hexaphyrin(1.0.1.0.0.0): An Expanded Porphyrin Ligand for the Actinide Cations Uranyl (UO22+) and Neptunyl (NpO2+)

Applications of actinide chemistry, whether for energy or defense purposes, have left a legacy of potential waste hazards. The new expanded porphyrin ligand 1 forms stable complexes with both uranyl (UO22+ ) and neptunyl (NpO2+ ) ions and presents a potential new avenue for waste remediation.

Catalytic Enantioselective Synthesis of α,β-Diamino Acid Derivatives

Highly enantio- and diastereoselective organocatalytic Mannich additions of alpha-isothiocyanato imides to sulfonyl imines are reported. Enantiomerically enriched syn-alpha,beta-diamino acid derivatives can be obtained in excellent yields using catalyst loadings as low as 0.25 mol %.