基于甲磺酰基的磺酰胺-氨醇作为催化醛的不对称炔基化反应新配体(英文)

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1、饪让糍2O1OChineseJournalofCatalysisV_01．3lNo．9文章编号：0253．9837(2010)09—1098．05国际版DOI：101016／S1872-2067(10)60106—4研究论文：1098～1102基于甲磺酰基的磺酰胺．氨醇作为催化醛的不对称炔基化反应新配体金薇，黄永波，万伯顺中国科学院大连化学物理研究所，辽宁大连I16023摘要：以商业易得的(一)一麻黄碱、(+)一伪麻黄碱和各种手性氨醇为主要原料，经过简单的两步反应，合成了一系列基于甲磺酰基的磺酰胺一氨醇(SAA)配体，并将其用于催化苯乙

2、炔基锌对醛的不埘称加成反应．在没有Ti(OiPr)等金属试剂的条件下，配体表现出较好的不对称诱导能力，取得了高达83％ee．关键词：磺酰胺一氨醇配体；不对称加成；炔基化反应；醛中图分类号：0643文献标识码：AMethylsulfonyl--BasedSulfamide--AmineAlcoholasaLigandforEnantioselectiveAlkynylationofAldehydesJINWei，HUANGYongbo，WANBoshunDalianInstituteofChemicalP}{vsics，ChineseAc

3、ademyofSciences,Dalian116023，Liaoning,ChinaAbstract：Chiralmethylsulfonyl—basedsulfamide—aminealcohol(SAA)ligandsweresynthesizedfromcommerciallyavailablestartingma—terialsintwosimplesteps．Methylsulfonyl—basedSAAligandscatalyzedtheasymmetricalkynylationofvariousaldehydesus

4、ingalkynylzinctoprovidechiralpropargylalcoholswithmoderatetogoodenantioselectivityupto83％ee．Keywords：sulfamide—aminealcohol；enantioselectiveaddition；alkynylation；aldehydeThecatalyticenantiOselectiveadditionofterminala1methanesulfonylrTObasedSAAwerealsoeffectiveforthekyne

5、stoaldehydesisaveryusefulmethodforthesynthesisasymmetricalkynylationofcarbonylcompounds[36-38]．ofchiralpropargylalcohols，whichareimportantversatileInordertounderstandtheelectronicandstericeffectsofbuildingblocksofmanybiologicallyactivecompoundsandchiralSAAonasymmetricalk

6、ynylationofaldehydesandasnaturalproducts[1_4]．Inrecentyears，chiralligands，suchpartofextendingtheapplicationofourSAAligands，weasN—methylephedrine[5，6]，sulfonamidealcohol[7，8]，reportmethylsulfonyl(Ms)一basedSAAcatalyzedenanti—BIN0Landitsderivativesf9—121，havesuccessfullybee

7、noselectivealkynylationofaldehydesunderverymildcondi—usedinthisreaction．However，Ti(O-'Pr)4orothermetaltionswithoutusingmoisturesensitiveTi(O-'Pr)4andspeciesareusuallynecessaryinmostofthesecatalyticsys—Zn(OTf1，．terns[13～17]．Ontheotherhand[18—32]，efficientligandsthatcanbep

8、reparedfromcheapandeasilyavailablestarting1Experimentamaterialsinafewsyntheticstepsandthataredesignedfo