硼氫化物不對稱還原酮制備旋光活性烯唑醇及烯效唑中手性氨基醇輔助劑的研究

1、南開大學碩士學位論文硼氫化物不對稱還原酮制備旋光活性烯唑醇及烯效唑中手性氨基醇輔助劑的研究姓名：唐奕龍申請學位級別：碩士專業(yè)：有機化學指導教師：唐除癡周正洪20030501南開大學黝屆碩士研霓生畢業(yè)論文Abstractnthisthesis，theasymmetricsynthesisofopticallyactiveSumisevenandDiniconazoleusingchiralaminoalcoholmodifiedboron

2、hydrideasthereductantwasstudiedFifteennewchiralaminoalcoholsweresynthesizedstartingfromsomereadilyavailablechiralsources，suchas()a—phenyIethylamine，Laminoacids，(十)一1一(4一nitrophenyl)2一amino一1，3propanedioletcThestructureso

3、fallthesepreparedcompoundswerecharacterizedby。lHNMRandelementalanalysisTheirapplicationasauxiliariesinboronhydridereductionofprochimlketoneswasinvestigatedThenatureofaminoalcoholWaSfoundtobeanessentialfactortoenantiosele

4、ctivityofthereactionGenerallytheauxiliarythatwasdisubstitutedonthecarbonaffachedtohydroxylgrouphadbetterchiralinductioneffectthanthatwasonlymonosubstitutedMoreoverbetlerresultswereobtainedwhenarylgroupinsteadofalkylgroup

5、wasintroducedtothecarbonaffachedtohydroxylgroupAdditionallytheintroductionofasub，stituent，especiallyanelectron—donatingmethylgroupatthepara—positionofthebenzeneringresultedinhigherenantioselectivityInmostcases，moderateen

6、antioselectivitywasobservedinthepresenceofchiralaminoalcoholsTheuseofaminoalcohol23derivedfromLprolineastheauxiliaryledtothebestresults(higherthan93％ee)ThereactiontemperaturehadasignificantinfluenceonthisreactionTheVield

7、andtheconversionofthereactionwereincreasedwiththeraiseofreactiontemperatureWhilechoosingdifferentreactionreagentduringtheabovesaidexperiment，itseemsthattherewerenuletofollowInaword，thereactionreagentdoeslittleinfluenceto