Thomas R. Verhoeven

Simple and efficient resolution of l,1′-bi-2-naphthol

Abstract Acetonitrile is a crucial solvent for a simple and efficient resolution of l,l′-bi-2-naphthol using N -benzylcincbonidium chloride. Both enantiomers can be easily obtained with ≥95% yield and ≥99% ee.

An Improved Procedure for Aromatic Cyanation

Abstract An effective method for conversion of aryl bromides to aryl cyanides is described. The procedure involves treatment of the aryl halide with zinc cyanide in the presence of a catalytic amount of palladium (0).

The behavior of indene oxide in the ritter reaction: A simple route to cis-aminoindanol

Abstract A regio- and stereoselective synthesis of cis-1-aminoindan-2-ol via a Ritter reaction is described.

THE ROLE OF 4-(3-PHENYLPROPYL)PYRIDINE N-OXIDE (P3NO) IN THE MANGANESE-SALEN-CATALYZED ASYMMETRIC EPOXIDATION OF INDENE

Abstract 4-(3-Phenylpropyl)pyridine N-Oxide (P 3 NO) has provided a more active and stable catalytic media for manganese-salen complex 1 in the asymmetric epoxidation of indene.

Synthesis of the 5-HT1D receptor agonist MK-0462 via a Pd-catalyzed coupling reaction

Abstract Application of a palladium-catalyzed coupling between 3 and 5a to the synthesis of the novel 5-HT 1D receptor agonist MK-0462 ( 1 ), a potential anti-migraine drug, is described.

A STUDY OF THE LITHIATION OF 2,6-DIBROMOPYRIDINE WITH BUTYLLITHIUM, AND ITS APPLICATION TO SYNTHESIS OF L-739,010

Mono-lithiation of 2,6-dibromopyridine by n-BuLi is complicated by deprotonation of the pyridine ring by the resulting mono-lithium species. This problem can be eliminated by a reverse addition, but this causes formation of the undesired dilithio species. However, rapid lithium-halogen exchange between 2,6-dibromopyridine and 2,6-dilithiopyridine produces 2-bromo-6-lithiopyridine cleanly. Thus, using reverse addition, the mono-lithiated pyridine can be generated in 98% yield.

The influence of ligand bite angle on the enantioselectivity of copper(II)-catalysed Diels–Alder reactions

Novel spirobis(oxazolines) provide excellent levels of stereocontrol in copper-catalysed Diels–Alder reactions; the larger the ligand bite angle the higher the enantioselection (up to 98.4% ee).

Application of indane-derived C2-symmetric bis(oxazolines) in two-point binding asymmetric Diels-Alder reactions

Abstract Bis(oxazolines) 1 –; 5 were examined in copper(II)-catalyzed asymmetric Diels-Alder reactions of acrylimide 6 and cyclopentadiene. Highly enantioselective reactions were attained with ligand 1 (up to 95% e.e.) as well as good endo selectivity (39:1) in the Cu(SbF 6 ) 2 -catalyzed process.

Application of a Ritter-type reaction to the synthesis of chiral indane-derived C2-symmetric bis(oxazolines)

Bis(oxazolines) 4, 6, 8, 9, 10, and 11 are prepared in a highly regio- and diastereo-selective manner from dinitriles and indanediol 3 in a Ritter-type reaction initiated by trifluoromethanesulfonic acid.

A conformational toolbox of oxazoline ligands

Abstract A toolbox of bis(oxazoline) and pyridinebis(oxazoline) ligands 6, 7, 8 has been used to probe conformational effects in Cu(II)-catalyzed Diels-Alder and Ru(II)-catalyzed cyclopropanation reactions.