Design and synthesis of chiral N-chloroimidodicarbonates: application to asymmetric chlorination of silyl enol ethers.
New chiral N-chloroimidodicarbonates, which function as efficient chiral chlorinating agents, were designed and synthesized. Among these, C(2)-symmetric (1R,2S,5R)-(-)-menthyl-N-chloroimidodicarbonate 2a provided moderate to good enantioselectivity (up to 40%) for the chlorination of silyl enol ethers to afford alpha-chloroketones only in the presence of a suitable Lewis acid such as Sm(OTf)(3).
Hajra
Saumen
S
Department of Chemistry, Indian Institute of Technology, Kharagpur, W.B. 721302, India. shajra@chem.iitkgp.ernet.in
Bhowmick
Manishabrata
M
Maji
Biswajit
B
Sinha
Debarshi
D