An organocatalytic asymmetric chlorolactonization.
A reagent controlled organocatalytic enantioselective chlorolactonization reaction has been developed. Several 4-aryl pentenoic acids were cyclized in the presence of 0.1 equiv of (DHQD)(2)PHAL, employing various N-chlorinated hydantoins as the terminal chlorenium source. Ten examples are presented with selectivities ranging from 43 to 90% ee. This work represents the first example of an enantioselective reagent-controlled chlorolactonization that approaches synthetically useful enantioselectivities.
Whitehead
Daniel C
DC
Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.
Yousefi
Roozbeh
R
Jaganathan
Arvind
A
Borhan
Babak
B
D002384:Catalysis; D003500:Cyclization; D005229:Fatty Acids, Monounsaturated / Q000737:chemistry*; D006827:Hydantoins / Q000737:chemistry; D006843:Hydrocarbons, Chlorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D005229:Fatty Acids, Monounsaturated; D006827:Hydantoins; D006843:Hydrocarbons, Chlorinated; D007783:Lactones; C009785:4-pentenoic acid