（4R）-（β-萘甲氧基）-（S）-脯氨酸催化的不對稱Aldol反應(yīng).pdf

1、蘇州大學(xué)碩士學(xué)位論文（4R）（β萘甲氧基）（S）脯氨酸催化的不對稱Aldol反應(yīng)姓名：陳五紅申請學(xué)位級別：碩士專業(yè)：有機(jī)化學(xué)指導(dǎo)教師：張雅文沈宗旋20040501(4RH戶蔡甲氧基H毋一脯氨陸健化的矸；對稱A|dol反應(yīng)摘要ABSTRACT1TheSynthesisofaNovelChiralPhase—transferCatalystCyclodipeptide(3S6S)一dibenzylpiperazine一2，5一dione，w

2、hichWaSpreparedinhighyieldbyheatingphenylalaninemethylesterdirectlywasreducedwitllNaBrh—BF3inDMEtogavethe(2sss)2，5一dibenzylpiperazine，whichwasreactedwithethylenebromideandtriethylamine，affording(2s5固一2，5bis(phenylmethyl)

3、一14一diazabicyclo[2，2，2]octaneUnexpectedlythepreparationofbisammoniumsaltwasunsuccessful2AsymmetricDirectAldolReactionspromotedby(4R)一(flNaphthalenyl)methoxy(S)proline(4R)hydroxy一(印prolinewasNprotectedbythereactionwithdit

4、ert—butylpyrocarbonatetogiveNBoc一(4R)一hydroxy(s)proline，whichwastremed、vithsodiumhydrideiⅡanhydroustetrahydrofuranandfollowedbyetherification淅til2bromomethyl—naphthalenetoformtheNBoo(4R)一儼Naphthalenyl)methoxy(固proline，wh

5、ichafterremovaloftheprotectinggroup晰也trifluoroaceticacid，gavethetitlecompound(4R)一(flNaphthalenyl)methoxy一(S)prolineThiscompoundCallserveasallefficientcatalystforthedirectasymmetricatdoladditionreactionofacetonetoavariet

6、yofaromaticaldehydeswithhighyields(6050／p957％)andgoodee’s(711％897％)BoththereactionyieldsandselectivitieswereobservedtobehigherthanthoseofthecorrespondingreactionscatalyzedbyprolineTheinfluencesoftheamountofthecatalyst，th

7、etemperatureandtheelectroniceffectsofthesubstrateswerediscussed，Keywords：phase—uansfercatalyst，DirectAldolreaction，chJ_ralcatalyst，aSymmetricsynthesis，(4R)一(finaphthalenyl)methoxy一(S)prolineWrittenby：ChenWuhongSupervised