Subscribe to RSS
Asymmetric Chlorination of Silyl Enol Ethers
S. Hajra*, M. Bhowmick, B. Maji, D. Sinha
Indian Institute of Technology, Kharagpur, India
23 August 2007 (online)
This paper reports a new chiral N-chloroimidodicarbonate ligand L1 which upon complexation to Sm(OTf)3 chlorinates silyl enol ethers to afford α-chloroketones in high yields and moderate ee values. It was found that in several cases the bulky TBDMS group gave consistently higher ee values than the smaller TMS group. The authors postulate that coordination of L1 to the Lewis acid produces the reactive syn-dipole conformer.