Chirospecific synthesis: Catalysis and chiral pool hand in hand

Koskinen, Ari M. P.

doi:10.1351/PAC-CON-10-10-09

Pure Appl. Chem., 2011, Vol. 83, No. 3, pp. 435-443

http://dx.doi.org/10.1351/PAC-CON-10-10-09

Published online 2011-01-16

Chirospecific synthesis: Catalysis and chiral pool hand in hand

Ari M. P. Koskinen

Department of Chemistry, Aalto University School of Science and Technology, P.O. Box 16100, FI-00076 Aalto, Finland

Abstract: Nature provides us with a wonderful pool of enantiopure starting materials for synthesis: amino acids, sugars, and many (but not all!) terpenes can be isolated even in large quantities in an uncompromised 100 % ee. Vicinal amino alcohols constitute a versatile group of organic structures; they are, in principle, available in enantiopure form from the chiral pool compounds or through chiral catalysis; they are potent intermediates for the synthesis of natural products and medicinally/biologically active compounds, and they provide a highly desirable scaffold for the construction of ligands for metals as well as organocatalysts. These new techniques will open up valuable new possibilities for the invention of new technologies for chemical synthesis, the desired course of chemical discoveries for the future. A robust entry to enantiopure vicinal amino alcohols from inexpensive naturally occurring amino acids has therefore become a key challenge for our endeavors in the development of methodology.