Application scope and limitations of TADDOL-derived chiral ammonium salt phase-transfer catalysts.

ABSTRACT: We have recently introduced a new class of chiral ammonium salt catalysts derived from easily available TADDOLs. To get a full picture of the scope of application and limitations of our catalysts we tested them in a variety of different important transformations. We found that, although these compounds have recently shown their good potential in the asymmetric α-alkylation of glycine Schiff bases, they clearly failed when we attempted to control more reactive nucleophiles like b-keto esters. On the other hand, when using them to catalyse the addition of glycine Schiff bases to different Michael acceptors it was found necessary to carefully optimize the reaction conditions for every single substrate class, as seemingly small structural changes sometimes required the use of totally different

SUBMITTER: Gururaja GN 

PROVIDER: S-EPMC4202194 | biostudies-literature | 2013 Apr

REPOSITORIES: biostudies-literature