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ORGANIC
LETTERS
HighlyEnantioselectiveMichaelAddition2007
Vol.9,No.3
ofCyclic1,3-DicarbonylCompoundsto413415
,-UnsaturatedKetones
Jian-WuXie,†,‡LeiYue,§WeiChen,§WeiDu,§JinZhu,†Jin-GenDeng,†and
Ying-ChunChen*,§,
KeyLaboratoryofAsymmetricSynthesisChirotechnologyofSichuanProinceand
UnionLaboratoryofAsymmetricSynthesis,ChengduInstituteofOrganicChemistry,
ChineseAcademyofSciences,Chengdu,China,KeyLaboratoryofDrug-Targetingof
EducationMinistryandDepartmentofMedicinalChemistry,WestChinaSchoolof
Pharmacy,SichuanUniersity,Chengdu610041,China,StateKeyLaboratoryof
Biotherapy,WestChinaHospital,SichuanUniersity,Chengdu,China,andGraduated
SchoolofChineseAcademyofSciences,Beijing,China
ycchenhuaxi@
ReceivedNovember7,2006
ABSTRACT
ThehighlyenantioselectiveMichaeladditionof1,3-cyclicdicarbonylcompoundsto,-unsaturatedketoneswasreportedtobecatalyzedby
anorganicprimaryaminederivedfromquinine.Achiralanticoagulantdrug,(S)-warfarin,wasdirectlypreparedin96%ee,andotherrelated
importantadductswerealsoobtainedinexcellentenantioselectivity(89−99%ee).
TheMichaeladditionto,-unsaturatedsystemsisanketonesevenatroomtemperature.4Inaninventiveexample,
importantcarboncar
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