Chiral Ligands Derived from Monoterpenes: Application in the Synthesis of Optically Pure Secondary Alcohols via Asymmetric Catalysis

被引:55
|
作者
Ibn El Alami, Mohammed Samir [1 ]
Amin El Amrani, Mohamed [1 ]
Agbossou-Niedercorn, Francine [2 ]
Suisse, Isabelle [2 ]
Mortreux, Andre [2 ]
机构
[1] Univ Abdelmalek Essaadi, Lab Chim Organ Appl, Fac Sci, Tetouan, Morocco
[2] Univ Lille Nord France, UMR CNRS 8181, UCCS, ENSCL, F-59652 Villeneuve Dascq, France
关键词
alcohols; asymmetric catalysis; chiral ligands; natural product synthesis; terpenes; HIGHLY ENANTIOSELECTIVE ADDITION; TRANSFER HYDROGENATION; BORANE REDUCTION; PROCHIRAL KETONES; AMINO-ALCOHOLS; N-OXIDES; STEREOSELECTIVE-SYNTHESIS; TERPENE AUXILIARIES; CARBONYL-COMPOUNDS; ALPHA-PINENE;
D O I
10.1002/chem.201404303
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The preparation of optically pure secondary alcohols in the presence of catalysts based on chiral ligands derived from monoterpenes, such as pinenes, limonenes and carenes, is reviewed. A wide variety of these ligands has been synthesized and used in several catalytic reactions, including hydrogen transfer, C-C bond formation via addition of organozinc compounds to aldehydes, hydrosilylation, and oxazaborolidine reduction, leading to high activities and enantioselectivities.
引用
收藏
页码:1398 / 1413
页数:16
相关论文
共 50 条
  • [41] Synthesis of chiral phosphine ligands with aromatic backbones and their applications in asymmetric catalysis
    Longmire, JM
    Zhang, XM
    TETRAHEDRON LETTERS, 1997, 38 (10) : 1725 - 1728
  • [42] The synthesis of new planar chiral heterobidentate chelate ligands for asymmetric catalysis
    Anderson, JC
    Osborne, J
    TETRAHEDRON-ASYMMETRY, 2005, 16 (05) : 931 - 934
  • [43] Chiral bidentate aminophosphine ligands: synthesis, coordination chemistry and asymmetric catalysis
    Zijp, EJ
    van der Vlugt, JI
    Tooke, DM
    Spek, AL
    Vogt, D
    DALTON TRANSACTIONS, 2005, (03) : 512 - 517
  • [44] ASYMMETRIC-SYNTHESIS VIA CHIRAL HYDROXYLAMINES - SYNTHESIS OF OPTICALLY PURE 4-SUBSTITUTED 2-AZETIDINONES
    BALDWIN, SW
    AUBE, J
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1983, 186 (AUG): : 179 - ORGN
  • [45] CONVENIENT SYNTHESIS OF LABILE OPTICALLY-ACTIVE SECONDARY ALKYL BROMIDES FROM CHIRAL ALCOHOLS
    HUTCHINS, RO
    MASILAMANI, D
    MARYANOFF, CA
    JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (06): : 1071 - 1073
  • [46] Synthesis and application of chiral phosphorus ligands derived from TADDOL for the asymmetric conjugate addition of diethyl zinc to enones
    Alexakis, A
    Burton, J
    Vastra, J
    Benhaim, C
    Fournioux, X
    van den Heuvel, A
    Levêque, JM
    Mazé, F
    Rosset, S
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2000, 2000 (24) : 4011 - 4027
  • [47] Design of a new class of chiral quinoline-phosphine ligands. Synthesis and application in asymmetric catalysis
    Delapierre, G
    Brunel, JM
    Constantieux, T
    Buono, G
    TETRAHEDRON-ASYMMETRY, 2001, 12 (09) : 1345 - 1352
  • [48] Synthesis of Cinchona Alkaloid Derived Chiral Squaramide Polymers by ADMET Polymerization and Their Application to Asymmetric Catalysis
    Ullah, Mohammad Shahid
    Itsuno, Shinichi
    CHEMISTRY LETTERS, 2018, 47 (09) : 1220 - 1223
  • [49] EFFICIENT ASYMMETRIC-SYNTHESIS OF OPTICALLY PURE TERTIARY MONO AND DIPHOSPHINE LIGANDS
    JUGE, S
    STEPHAN, M
    LAFFITTE, JA
    GENET, JP
    TETRAHEDRON LETTERS, 1990, 31 (44) : 6357 - 6360
  • [50] Application of sharpless asymmetric dihydroxylation to synthesis of chiral β-amino alcohols
    Liu, WM
    Liu, XY
    Song, RJ
    Zhang, SY
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2006, 26 (03) : 341 - 345