β-Siloxy-α-haloketones through highly diastereoselective single and double mukaiyama aldol reactions.

Abstract

Double-action haloketones: A super silyl group enabled the first highly diastereoselective Mukaiyama aldol reactions of α-chloro- and α-fluoroketones with a wide range of aldehydes, providing anti-β-siloxy-α-haloketones. This process is compatible with one-pot double-aldol methodology and allows for rapid access to new halogen-modified polyketide fragments bearing up to four contiguous stereocenters.