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PublishedonWeb07/22/2003
AsymmetricAdditionofAlkylzincReagentstoCyclic,-Unsaturated
KetonesandaTandemEnantioselectiveAddition/Diastereoselective
EpoxidationwithDioxygen
Sang-JinJeonandPatrickJ.Walsh*
P.RoyandDianeT.VagelosLaboratories,DepartmentofChemistry,UniersityofPennsylania,
231South34thStreet,Philadelphia,Pennsylania19104-6323
ReceivedMay23,2003;E-mail:pwalsh@
WerecentlyreportedtheasymmetricadditionofalkylzincTable1.AsymmetricAdditionofAlkylGroupstoCyclicEnones
reagentstoketonesusinganeasilypreparedconstrained-geometry
catalyst.1Anoteworthyaspectofthisstudyisthatitoffersasolution
toalong-standingprobleminsyntheticorganicchemistry:the
catalyticsynthesisoftertiaryalcoholsfromacetophenonederivatives
withhighenantioselectivity.Incontrasttorelatedadditionreactions
withaldehydesubstrates,whicharepromotedbyhundredsof
catalysts,2,3onlyahandfulofsystemswillpromoteadditionsto
ketones,1,47andmostoftheserequirehighcatalystloadingsand
longreactiontimes.57Despitesignificanteffortinthisarea,we
arenotawareofsuccessfulreportsoftheenantioselectiveaddition
ofalkylgroupstoconjugatedcyclicenones.InthisCommunication,
wereporttheresultsofaninvestigationintotheefficientandhighly
enantioselective1,2-additionreactionsofcyclic,-unsaturated
ketones.Theresultingtertiaryallylicalcoholsarevaluableinter-
mediatesthatcanbefurtherelaboratedviadirectedepoxidation
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