Unprecedented, fully recyclable, solid-supported reagent for the kinetic resolution of racemic amines through enantioselective N-acetylation

被引:14
作者
Arseniyadis, S
Subhash, PV
Valleix, A
Wagner, A
Mioskowski, C
机构
[1] Univ Louis Pasteur Strasbourg 1, Fac Pharm, CNRS, Lab Synth Bioorgan, F-67401 Illkirch Graffenstaden, France
[2] CEA Saclay, Dept Biol Cellulaire & Mol, Serv Mol Marquees, F-91191 Gif Sur Yvette, France
关键词
D O I
10.1039/b504200c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The high-yielding synthesis and application of the first polymer supported reagent for the kinetic resolution (KR) of amines through enantioselective acetylation is described; this new supported chiral reagent allows the KR of primary amines with excellent selectivities at room temperature; moreover, this supported approach is highly efficient as the Merrifield-supported chiral scaffold can be quantitatively recovered and recycled.
引用
收藏
页码:3310 / 3312
页数:3
相关论文
共 20 条
  • [1] 3-(N,N-diacylamino)quinazolin-4(3H)-ones as enantioselective acylating agents for amines
    Al-Sehemi, AG
    Atkinson, RS
    Fawcett, J
    Russell, DR
    [J]. TETRAHEDRON LETTERS, 2000, 41 (13) : 2239 - 2242
  • [2] Arai S, 2001, ANGEW CHEM INT EDIT, V40, P234, DOI 10.1002/1521-3773(20010105)40:1<234::AID-ANIE234>3.0.CO
  • [3] 2-K
  • [4] Tuning the enantioselective N-acetylation of racemic amines: A spectacular salt effect
    Arseniyadis, S
    Subhash, PV
    Valleix, A
    Mathew, SP
    Blackmond, DG
    Wagner, A
    Mioskowski, C
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (17) : 6138 - 6139
  • [5] Kinetic resolution of amines: A highly enantioselective and chemoselective acetylating agent with a unique solvent-induced reversal of stereoselectivity
    Arseniyadis, S
    Valleix, A
    Wagner, A
    Mioskowski, C
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (25) : 3314 - 3317
  • [6] POLYMER-SUPPORTED SYNTHESIS OF CYCLIC ETHERS - ELECTROPHILIC CYCLIZATION OF TETRAHYDROFUROISOXAZOLINES
    BEEBE, X
    CHIAPPARI, CL
    OLMSTEAD, MM
    KURTH, MJ
    SCHORE, NE
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (13) : 4204 - 4212
  • [7] Facile solid phase synthesis of an activated diazo linker
    Bhalay, G
    Dunstan, AR
    [J]. TETRAHEDRON LETTERS, 1998, 39 (42) : 7803 - 7806
  • [8] Bhalay G, 2000, SYNLETT, P1846
  • [9] Nucleophilic chiral amines as catalysts in asymmetric synthesis
    France, S
    Guerin, DJ
    Miller, SJ
    Lectka, T
    [J]. CHEMICAL REVIEWS, 2003, 103 (08) : 2985 - 3012
  • [10] A new benchmark for the non-enzymatic enantioselective acylation of amines: use of a planar-chiral derivative of 4-pyrrolidinopyridine as the acylating agent
    Ie, Y
    Fu, GC
    [J]. CHEMICAL COMMUNICATIONS, 2000, (02) : 119 - 120