On the chlorenium source in the asymmetric chlorolactonization reaction.
N-Acylated N-chlorohydantoins are shown to be competent chlorenium sources in the (DHQD)(2)PHAL-mediated asymmetric chlorolactonization. The derivatives demonstrate the exact role of the N1 and N3 chlorine atoms in the parent dichlorohydantoins with the N1 chlorine serving as an inductive activator and the N3 chlorine being delivered to the substrate. The putative associated catalyst/chlorine source complex was experimentally demonstrated through a series of matched/mismatched experiments employing chiral N-chlorinated hydantoins.
Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.
Roozbeh
R
Yousefi
Daniel C
DC
Whitehead
Janet M
JM
Mueller
Richard J
RJ
Staples
Babak
B
Borhan