A dynamic kinetic asymmetric transformation in the alpha-hydroxylation of racemic malonates and its application to biologically active molecules

Reddy, D.Sudhakar.; Shibata, N.; Nagai, J.; Nakamura, S.; Toru, T.

Angewandte Chemie 48(4): 803-806

ISSN/ISBN: 1521-3773

2009

PMID: 19101968

DOI: 10.1002/anie.200804476

Document: 001900209

Sly like a “DBFOX”: The chiral α-hydroxy malonate 2 can be prepared in high yield and with up to 98 % ee from racemic malonate 1 through α-hydroxylation using oxaziridine 3 and is catalyzed by the (R,R)-DBFOX-Ph/Ni II complex (see scheme). Biologically useful molecules have been prepared by using this method and illustrate its efficiency.