Enantio- and diastereoselective Ir-catalyzed allylic substitutions for asymmetric synthesis of amino acid derivatives

被引：153
作者：
Kanayama, T [1 ]
Yoshida, K [1 ]
Miyabe, H [1 ]
Takemoto, Y [1 ]
机构：
[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 606, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 18期
关键词：
allylation; amino acids; enantioselectivity; iridium; P ligands;
D O I：
10.1002/anie.200250654
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Simply switching the base employed in the first enantioselective allylic substitutions of diphenylimino glycinate 1 with 2, which are catalyzed by an Ir complex of chiral phosphite 5, allows the two branched diastereomers 3 and 4 to be selectively synthesized with little or no formation of linear substitution products.
引用
收藏
页码：2054 / 2056
页数：3
相关论文
共 57 条
  • [1] [Anonymous], ANGEW CHEM
  • [2] [Anonymous], ANGEW CHEM
  • [3] Enantioselective catalysis using phosphorus-donor ligands containing two or three P-N or P-O bonds
    Ansell, J
    Wills, M
    [J]. CHEMICAL SOCIETY REVIEWS, 2002, 31 (05) : 259 - 268
  • [4] Structural control in palladium(II)-catalyzed enantioselective allylic alkylation by new chiral phosphine-phosphite and pyridine-phosphite ligands
    Arena, CG
    Drommi, D
    Faraone, F
    [J]. TETRAHEDRON-ASYMMETRY, 2000, 11 (13) : 2765 - 2779
  • [5] ALPHA-AMINO ESTER DERIVATIVES AS NUCLEOPHILES IN STEREOSELECTIVE PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION-REACTIONS
    BALDWIN, IC
    WILLIAMS, JMJ
    BECKETT, RP
    [J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (07) : 1515 - 1518
  • [6] Ir-catalysed allylic substitution: mechanistic aspects and asymmetric synthesis with phosphorus amidites as ligands
    Bartels, B
    Helmchen, G
    [J]. CHEMICAL COMMUNICATIONS, 1999, (08) : 741 - 742
  • [7] Blacker AJ, 2000, CHEM-EUR J, V6, P353, DOI 10.1002/(SICI)1521-3765(20000117)6:2<353::AID-CHEM353>3.0.CO
  • [8] 2-U
  • [9] Palladium-catalyzed allylic alkylation of tert-butyl(diphylmethylene)-glycinate with simple allyl esters under chiral phase transfer conditions
    Chen, GS
    Deng, YJ
    Gong, LZ
    Mi, AQ
    Cui, X
    Jiang, YZ
    Choi, MCK
    Chan, ASC
    [J]. TETRAHEDRON-ASYMMETRY, 2001, 12 (11) : 1567 - 1571
  • [10] New chiral phosphine-phosphite ligands in the enantioselective palladium-catalyzed allylic alkylation
    Deerenberg, S
    Schrekker, HS
    van Strijdonck, GPF
    Kamer, PCJ
    van Leeuwen, PWNM
    Fraanje, J
    Goubitz, K
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16) : 4810 - 4817
123456