Diastereoselective alkylation reactions employing a new camphor-based 2-phenylimino-2-oxazolidine chiral auxiliary
Diastereoselective alkylation reactions employing a new camphor-based 2-phenylimino-2-oxazolidine chiral auxiliary
摘要
A new camphor-based 2-phenylimino-2-oxazolidine chiral auxiliary was prepared and it was shown to be a particularly effective chiral auxiliary for asymmetric alkylations affording high yields and diastereoselectivities. The alkylation products were readily cleaved by simple alkaline hydrolysis to give a-alkylated carboxylic acids in good yield and in almost enatiomerically pure form.
A new camphor-based 2-phenylimino-2-oxazolidine chiral auxiliary was prepared and it was shown to be a particularly effective chiral auxiliary for asymmetric alkylations affording high yields and diastereoselectivities. The alkylation products were readily cleaved by simple alkaline hydrolysis to give a-alkylated carboxylic acids in good yield and in almost enatiomerically pure form.
基金
the National Natural Sciences Foundation of China(No.21342002)
2011 National Major Scientific Instrument and Equipment Development Project(No.2011YQ12003505)for financial support
参考文献9
-
1JianChaoLIU YuSheYANG RuYunJI.A Convenient Method for the Asymmetric Synthesis of KAD-1229[J].Chinese Chemical Letters,2005,16(4):430-432. 被引量：2
-
2JiaChengNING ShuMAO YeDiGUAN.Asymmetric Synthesis of α-Substituted-γ-butyrolactone Empolying Prolinol Type of Auxiliaries[J].Chinese Chemical Letters,2005,16(1):17-19. 被引量：1
-
3Ji-Shu Zhang,Cui-Fen Lu,Zu-Xing Chen,Yan Li,Gui-Chun Yang.Boron enolates of a hydantoin chiral auxiliary derived from l -phenylalanine: a versatile tool for asymmetric aldol reactions[J].Tetrahedron: Asymmetry.2012(1)
-
4Gopal Khatik,Ravi Khurana,Varun Kumar,Vipin Nair.Asymmetric Induction by (S)-4-Isopropyl-1-phenylimidazolidin-2-thionein Titanium-Mediated Aldol Reactions and Its Application in Enantioselective Synthesisof (R)-Baclofen[J].Synthesis.2011(19)
-
5Fabien Fécourt,Gérald Lopez,Arie Van Der Lee,Jean Martinez,Georges Dewynter.Cyclosulfamide as a chiral auxiliary: application to efficient asymmetric synthesis (alkylation/aldolization)[J].Tetrahedron: Asymmetry.2010(19)
-
6Jesús M. García,José M. Odriozola,Ainara Lecumberri,Jesús Razkin,Alberto González.A concise and efficient route to the Alzheimer’s therapeutic agent ( R )-arundic acid[J].Tetrahedron.2008(47)
-
7Tomoya Kotake,Yoshio Hayashi,S. Rajesh,Yoshie Mukai,Yuka Takiguchi,Tooru Kimura,Yoshiaki Kiso.Design and synthesis of a new polymer-supported Evans-type oxazolidinone: an efficient chiral auxiliary in the solid-phase asymmetric alkylation reactions[J].Tetrahedron.2005(15)
-
8Gue-Jae Lee,Taek Hyeon Kim,Jae Nyoung Kim,Uk Lee.l -Valinol and l -phenylalaninol-derived 2-phenylamino-2-oxazolines as chiral auxiliaries in asymmetric alkylations[J].Tetrahedron: Asymmetry.2002(1)
-
9Claudio Palomo,Mikel Oiarbide,Alberto Gonaz’alez,Jesús M. García,Fabienne Berrée.Exo , exo -2,3-Diaminoborneol-derived imidazolidinone as chiral auxiliary for asymmetric alkylations[J].Tetrahedron Letters.1996(26)
二级参考文献22
-
1E J Corey, X M Cheng, The Logic of Chemical Synthesis, John Weily & Sons Inc, 1989,244-268.
-
2A I Meyers, E D Mihelich, J Org Chem, 1975, 40, 1186.
-
3A I Meyers, et al, J Org Chem, 1980, 451 2792.
-
4D A Evans, J M Takacs, Tetrahydron Lett, 1980, 21, 4233.
-
5E. J. Corey, X. M. Cheng, The Logic of Chemical Synthesis, John Weily & Sons Inc., 1989,244-268.
-
6A. I. Meyers, E. D. Mihelich, J. Org. Chem., 1975, 40, 1186.
-
7A. I. Meyers, et al., J. Org. Chem., 1980, 45, 2792.
-
8D. A. Evans, J. M. Takacs, Tetrahydron Lett., 1980, 21, 4233.
-
9W. Oppolzer, R. Moretti, S. Thomi, Tetrahedron Lett., 1989, 30, 5603.
-
10H. Heitsch, R. Henning, H. W. Kleemann, et al., J. Med. Chem., 1993, 36, 2788.
-
1刘晓岚,刘永红,石尧成,菅盘名.希夫碱在有机合成中的应用研究[J].有机化学,2002,22(7):482-488. 被引量：63
-
2Su Yun Liu,Shigeo Katsumura.An improved synthesis of (-)-7-isopropyl-cis-l-amino-2-indanol the chiral auxiliary for 6π-azaelectrocyclization[J].Chinese Chemical Letters,2009,20(10):1204-1206.
-
3Zheng Ning LI,Zhi Xiu XU,Zhuo ZHENG,Hut Lin CHEN(Dalian Institute of Chemical Physics, the Chinese Academy of Sciences, Dalian 116023).Synthesis of Chiral 3-Acylcamphors[J].Chinese Chemical Letters,1999,10(5):347-348.
-
4吕士杰,姜茹,周宏英,郑燕,傅宏祥.新型手性β－氨基醇用于不对称催化醛类烷基化反应[J].分子催化,1995,9(5):358-362. 被引量：2
-
5陈爱军,王振雷,刘全忠.新型相转移催化剂的合成与催化性能研究[J].西华师范大学学报（自然科学版）,2008,29(2):168-172. 被引量：1
-
6李春,李伟逊,许胜,段伟良.钯催化甲基苯基膦氢的不对称烷基化反应合成含膦手性中心化合物[J].有机化学,2013,33(4):799-802. 被引量：1
-
7刘永红,刘晓岚.羰基化合物α—碳的不对称烷基化研究进展[J].天水师范学院学报,1995,15(0):36-57.
-
8W.H.Chan,A.W.M.Lee.New Chiral Norbornenesultam as the Chiral Auxiliary in Asymmetric Alkylation[J].厦门大学学报（自然科学版）,1999,38(S1):211-211.
-
9YÜKSEKTEPE Çigdem,ÖZKAN Hamdi,YAVUZ Serkan,YANMAZ Volkan,DISLI Ali,BÜYÜKGÜNGÖR Orhan.Synthesis, Crystal and Molecular Structure and Biological Activity of Dimethyl Trans-3-(2-bromophenyl)-2-methylisoxazolidine-4,5-dicarboxylate[J].Chinese Journal of Structural Chemistry,2012,31(9):1251-1262.
-
10WANG Jing-xia,CHEN Yu,XU Xiao-hong,CAI Rui-fang,HUANG Zu-en.Lithium Camphor initiated Anionic Polymerization of C_(60) and Styrene[J].Chemical Research in Chinese Universities,1999,15(4):354-357.
