Highly chemoselective addition of amines to epoxides in water.

Oxidative amidation and azidation of aldehydes by NHC catalysis.

Tributylphosphine was found to be an effective promoting reagent for the ring-opening reaction of various epoxides and aziridines with nucleophile to produce corresponding anti-bifunctional products in moderate to excellent yields in water.

Efficient ring-opening reaction of epoxides and aziridines promoted by tributylphosphine in water.

Commercially available zinc(II) perchlorate hexahydrate [Zn(ClO4)2·6H2O] was found to be a new and highly efficient catalyst for opening of epoxide rings by amines affording 2-amino alcohols in high yields under solvent-free conditions and with excellent chemo-, regio-, and stereoselectivities. For unsymmetrical epoxides, the regioselectivity was influenced by the electronic and steric factors associated with the epoxides and the amines. A complementarity in the regioselectivity was observed during the reaction of styrene oxide with aromatic and aliphatic amines:  aromatic amines provided amino alcohols from nucleophilic attack at the benzylic carbon as major products whereas aliphatic amines resulted in formation of the amino alcohols through reaction at the terminal carbon atom of the epoxide ring as the major/sole products. Reaction of aniline with various glycidic ethers gave the amino alcohols by regioselective nucleophilic attack at the terminal carbon atom of the epoxide ring as the only/major prod...

Zinc(II) perchlorate hexahydrate catalyzed opening of epoxide ring by amines: applications to synthesis of (RS)/(R)-propranolols and (RS)/(R)/(S)-naftopidils.

Udayan Das

Papers

Facile ring opening of oxiranes with aromatic amines in fluoro alcohols

Facile Ring Opening of Oxiranes with Aromatic Amines in Fluoro Alcohols.