叔醇α-羥基膦酸酯的不對(duì)稱合成及靛紅的Vinylogous Mukaiyama Aldol反應(yīng)研究.pdf

1、南開大學(xué)碩士學(xué)位論文叔醇α羥基膦酸酯的不對(duì)稱合成及靛紅的VinylogousMukaiyamaAldol反應(yīng)研究姓名：孔莎莎申請(qǐng)學(xué)位級(jí)別：碩士專業(yè)：有機(jī)化學(xué)指導(dǎo)教師：陳茹玉201205AbstractAbstractOverthepastyears，organocatalystsbearinghydrogenbondingactivatinggrouparethesubjectsofintensiveresearch，nledouble

2、hydrogenbondinginteractionofNH—ofurea／thioureaandreactanthasbeengenerallyrealizedtohaveaspecificroleintheefficientcatalysisandhighenantiocontr01So，organocatalysishasbecomeanimportantprotocolinthefieldofasymmetriccatalysi

3、sThisdissertationincludesthreeparts：(1)Inthefistpartofthedissertation，therecentprogressonurea／thioureacatalyzedstereoselectivereactionshasbeensummarizedAndthenaseriesofchiralbifunctionalthioureaorganocatalystsweredesigne

4、dandsynthesizedWehopedtofindexcellentcatalystswimpotentcatalystsefficiencyandhighenantiocontrolthroughtuningthechiralaminebackbonesorthesterichindranceeffectofthegrouponthioureamoiety(2)Wrecarriedouttheenantioselectivead

5、ditionoftrimethylsilylcyanide(TMSCN)withacylphosphonatestoproducetertiaryahydroxyphosphonates111ereactionWasproceededbyusingchiralbifunctionaltertiaryaminethioureaascatalystandP—nitrophenolasadditiveintoluene髂solventat78

6、oCToourdelightproductsCallbeobtainedwithratiosofenantiomershigherthan99％。Thisprocedureprovidesarapidaccesstobiologicallyimportanttertiaryahydroxyphosphonates碭estructurewasconfirmedbyX—raydiffractionanalysisandthestructur

7、eshowedthattheabsoluteconfigurationoftheahydroxyphosphonateproductWasassignedas墨111ecompounds’structureswereconfirmedby1HNMR，13CNMR，”PNMR，ESIMSandHRMS(3)WereportedthediastereoselectiveprotocolforcatalyticMukaiyamaAldolRe

8、action(MAR)ofisatinwith2(trimethylsilyloxy)furanbyusingquinineascatalyst11healdolreactionof2(trimethylsilyloxy)furanwithisatinunderwentsmoothlyinthepresenceofquinineintolueneassolventat78oCandresultedintoaldoladductsinhi