Development of a Practical Synthetic Method for N-tert-Butoxycarbonyl α-Ketimino Esters

被引:12
作者
Hashimoto, Takuya [1 ]
Yamamoto, Kumiko [1 ]
Maruoka, Keiji [1 ]
机构
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
关键词
ASYMMETRIC-SYNTHESIS; CONSTRUCTION; KETONES; AMINES;
D O I
10.1246/cl.2011.326
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Despite the potential synthetic utility of N-Boc alpha-ketimino esters as prochiral ketimines to give chiral alpha-tertiary amines, there has been no general method to access these molecules in a practical fashion. We report herein a procedure for the one-step synthesis of N-Boc alpha-ketimino esters starting from the corresponding alpha-keto esters.
引用
收藏
页码:326 / 327
页数:2
相关论文
共 17 条
[1]   Electrophilic amination of enolates with oxaziridines: effects of oxaziridine structure and reaction conditions [J].
Armstrong, A ;
Edmonds, ID ;
Swarbrick, ME ;
Treweeke, NR .
TETRAHEDRON, 2005, 61 (35) :8423-8442
[2]   Recent progress on the stereoselective synthesis of acyclic quaternary α-amino acids [J].
Cativiela, Carlos ;
Diaz-de-Villegas, Maria D. .
TETRAHEDRON-ASYMMETRY, 2007, 18 (05) :569-623
[3]   SILICON-ASSISTED SYNTHESIS OF BETA-LACTAMS [J].
COLVIN, EW ;
MCGARRY, D ;
NUGENT, MJ .
TETRAHEDRON, 1988, 44 (13) :4157-4172
[4]   The catalytic asymmetric strecker reaction: Ketimines continue to join the fold [J].
Connon, Stephen J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (07) :1176-1178
[5]   Enantioselective catalytic formation of quaternary stereogenic centers [J].
Cozzi, Pier Giorgio ;
Hilgraf, Robert ;
Zimmermann, Nicole .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (36) :5969-5994
[6]   TRIFLUOROALANINE N-CARBOXY ANHYDRIDE - A REACTIVE INTERMEDIATE FOR THE SYNTHESIS OF LOW SURFACE-ENERGY POLYPEPTIDES [J].
DESSIPRI, E ;
TIRRELL, DA .
MACROMOLECULES, 1994, 27 (19) :5463-5470
[7]   PREPARATION OF PRIMARY AMINES AND 2-AZETIDINONES VIA N-TRIMETHYLSILYL IMINES [J].
HART, DJ ;
KANAI, K ;
THOMAS, DG ;
YANG, TK .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (03) :289-294
[8]   Asymmetric Trisubstituted Aziridination of Aldimines and Ketimines using N-α-Diazoacyl Camphorsultams [J].
Hashimoto, Takuya ;
Nakatsu, Hiroki ;
Yamamoto, Kumiko ;
Watanabe, Shogo ;
Maruoka, Keiji .
CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (02) :607-613
[9]   Synthesis and pharmacology of glutamate receptor ligands: New isothiazole analogues of ibotenic acid [J].
Jørgensen, Charlotte G. ;
Clausen, Rasmus P. ;
Hansen, Kasper B. ;
Bräuner-Osborne, Hans ;
Nielsen, Birgitte ;
Bjorn Metzler ;
Kehler, Jan ;
Krogsgaard-Larsen, Povl ;
Madsen, Ulf .
Organic and Biomolecular Chemistry, 2007, 5 (03) :463-471
[10]  
KUPFER R, 1984, SYNTHESIS-STUTTGART, P688