1. On the Chlorenium Source in the Asymmetric Chlorolactonization Reaction.
- Author
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Roozbeh Yousefi, Daniel C. Whitehead, Janet M. Mueller, Richard J. Staples, and Babak Borhan
- Subjects
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ASYMMETRIC synthesis , *LACTONES , *CHLORINE , *CHEMICAL reactions , *HYDANTOIN , *ACTIVATION (Chemistry) , *CATALYSIS - Abstract
N-Acylated N-chlorohydantoins are shown to be competent chlorenium sources in the (DHQD)2PHAL-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. [ABSTRACT FROM AUTHOR]
- Published
- 2011
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