手性亚磺酰胺催化不对称硅氢化合成手性β-氨基膦酸酯.pdf

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1、第24卷第l2期化学研究与应用Vo1．24，No．122012年12月ChemicalResearchandApplicationDee．，2012文章编号：1004-1656(2012)12—1840-05Asymmetricsynthesisofchiral-aminophosphonatesviahydrosflylationcatalyzedbychiralsulfinamideFANGHui．一，CAIXian-rong，SUNJian’’(1．NaturalProductsResearchCenter，ChengduInstituteo

2、fBiology，ChineseAcademyofSciences，Chengdu610041，China；2．GraduateSchoolofChineseAcademyofSciences，Beijing100039，China)AbstractiThefirstorganocatalytiemethodhadbeendevelopedfortheasymmetricreductionoffl-aminophosphonatesusingchiralsulilnamidesascatalystandtriehlorosilane鹊reducin

3、gagent，whichfurnishedtheusefulproductsehiral·aminophosphonateswithhig}lyieldsandg0odenantioselectivities．Keywords：#-aminophosphonate；asymmetrichydresilylation；trichlorosilane；organocatalysis；enantioselectivity中图分类号：0627．5文献标识码：A手性亚磺酰胺催化不对称硅氢化合成手性一氨基膦酸酯方辉2，蔡显荣，孙健h(1．中国科学院成都生物研究

4、所，四川成都610041；2．中国科学院研究生院，北京100039)关键词：以手性亚磺酰胺作为催化剂，三氯硅烷为还原剂，发展了通过有机小分子催化合成有用的手性氨基膦酸酯的方法，获得了较好的产率和对映选择性。中图分类号：届-氨基膦酸酯；不对称硅氢化；三氯硅烷；有机催化；对映选择性Chiral卢-aminophosphonicacidsandtheirde-Bemeretalreportedthefirstcatalyticmethodthatrivativesareanimportantclassofcompounds，whichpromotedth

5、easymmetrichydrogenationof—enaminohavebeenfrequentlyusedashioisosteresofaminophosphonateswithhighyieldsandenanfioselectivitiesacidsinthedesignofbiochemicallyandpharmaceuti-(<92％8e)usingchiralRh．complexascatalyst．callyusefulmolecules[剖．Recently，increasingefortsLater，theenantios

6、electivityofthistransformationWaShadconcentratedonthedevelopmentofmethodsforfurtherimprovedupto>99％eebytheuseofsimilarthesynthesisofchiral届-aminophosphonates⋯．Cata-butmorepowerfulcatalystsbyDoherty[。]andChavez[¨]lyticasymmetricreductionoffl-enaminophosphonates．ToOUrbestknowled

7、ge，sofartherehadconstitutedamoststraightforwardapproachtoenanti—beennometal-freeorganocatalyticmethodsreportedomericallypure·aminophosphonates，which，howev-intheliteraturethatcouldellableenantiose1ectivere．er，hadonlygaveraresuccessfulexamples．In2008，ductionoffl—enaminophosphona

8、tesfortheproduction收稿日期：2012-05-08；修回侣期：2012-06-07基金项目：国家自然科学