Catalytic asymmetric detrifluoroacetylative aldol reactions of aliphatic aldehydes for construction of C-F quaternary stereogenic centers

We demonstrate, that the reactions of in situ generated fluoro-enolates with a range of aliphatic aldehydes can be successfully performed using asymmetric catalyst derived from chiral ligand and Cu (OTf)(2). The enantioselectivity of the formation of two contiguous stereogenic carbons in these additions was excellent, rendering the developed approach as an important methodological advance in asymmetric catalytic reactions of detrifluoroacetylatively generated fluoro-enolates. This process allows preparation of structurally new pharmaceutically interesting class of 1,3-hydroxy ketones containing C-F quaternary stereogenic center adjacent to secondary hydroxy group. (C) 2016 Elsevier B.V. All rights reserved.