5,5-二苯基-4-(S)-(对羟基)苄基噁唑烷酮的合成

Synthesis of 5,5-diphenyl-4-(S)-(p-hydroxyl)benzyl oxazolidinone

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摘要以价廉易得的天然L-酪氨酸为原料经4步反应合成了5,5-二苯基-4-(S)-(对羟基)苄基唑烷酮,产率32%,经IR,1HNMR,13CNMR及MS等检测均与其结构相符,并对合成路线中的关环方法进行了初步研究. 5,5-diphenyl-4-(S)-(p-hydroxyl)benzyl oxazolidinone was synthesized by L-tyrosine via 4 steps in high yield(32?%). The structure of target molecule was detected by IR,~1H NMR,^(13)C NMR and MS.The method of cyclization was also discussed.

作者万亚东杨桂春陈祖兴

机构地区湖北大学化学与材料科学学院

出处《湖北大学学报（自然科学版）》 CAS 北大核心 2005年第2期149-151,共3页 Journal of Hubei University：Natural Science

基金国家自然科学基金(No:20372019)资助项目

关键词 L-酪氨酸合成 5 5-二苯基取代噁唑烷酮手性助剂 L-tyrosine synthesis 5,5-diphenyl oxazolidinone chiral auxiliary

分类号 O64 [理学—物理化学]

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1Ager D J, Prakash I, Schaad D R. 2-Amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis[J]. Chem Rev, 1996,96:835～875.
2Gibson C L,Gillon K,Cook S.A study of 4-substituted 5,5-diaryl oxazolidin-2-ones as efficacious chiral auxiliaries[J].Tetrahedron Lett,1998,39:6733～6736.
3Faita G,Paio A,Quadrelli P,et al.Solid supported chiral auxiliaries in asymmrtric synthesis (Part 2): catalysis of 1,3-dipolar cycloadditions by Mg(Ⅱ) cation[J].Tetrahedron,2001,57:8313～8322.
4Itsuno S, Nakano M, Ito K. Asymmetric synthesis using chirally modified borohydrides(Part 4):enantioselective reduction of ketones and oxime ethers with the regent prepared from borane and polymer-supported (S)-(-)-2-amino-3-(p-hydroxyphenyl) -1,1-diphenyl-propan-1-ol[J].J Chem Soc Perkin Trans ,1985,1:2615～2619.
5Gaul G, Schweizer B W, Seiler P, et al. Crystal structures-a manifesto for the superiority of the valine-derived 5,5-diphenyloxazolidinone as auxiliary in enantioselective organic synthesis [J].Helvetica Chimica Acta,2002,85:1546～1566.
6Sibi M P,Deshpande P K,Ji J.A new chiral oxazolidinone derived from diphenylalaninol,Aldol,alkylation and Diels-Alder reactions[J].Tetrahedron Lett,1995,36:8965～8968.
7Phoon C W,Abell C.Solide phase aldol and conjugaten addition reactions using evans' oxazolidinone chiral auxiliary[J].Tetrahedron Lett,1998,39:2655～2658.

1石炜,段月姣,阚洪柱,杨琍苹,胡文浩.(S)-4-苄基-2-噁唑烷酮的合成工艺改进[J].合成化学,2010,18(4):490-492.
2汪毓海,陈庆华.嘌呤、嘧啶类新手性化合物的合成[J].中国科学（B辑）,1998,28(6):531-539. 被引量：34

湖北大学学报（自然科学版）

2005年第2期

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5,5-二苯基-4-(S)-(对羟基)苄基噁唑烷酮的合成

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