Asymmetric synthesis of tertiary thiols and thioethers

被引:180
|
作者
Clayden, Jonathan [1 ]
MacLellan, Paul [1 ]
机构
[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England
关键词
asymmetric synthesis; organolithium; sulfur; substitution; thiol; OXIDATION-REDUCTION CONDENSATION; ALKYL ARYL SULFIDES; HIGHLY ENANTIOSELECTIVE REACTIONS; STEREOCHEMICAL COURSE; ALPHA-ARYLATION; CONFIGURATIONAL STABILITY; STEREOSPECIFIC SYNTHESIS; ENANTIOMERICALLY PURE; CARBOXYLIC-ACIDS; BOND FORMATION;
D O I
10.3762/bjoc.7.68
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enantiomerically pure tertiary thiols provide a major synthetic challenge, and despite the importance of chiral sulfur-containing compounds in biological and medicinal chemistry, surprisingly few effective methods are suitable for the asymmetric synthesis of tertiary thiols. This review details the most practical of the methods available.
引用
收藏
页码:582 / 595
页数:14
相关论文
共 50 条
  • [41] Kinetics and mechanism of complex formation between [PtCl(DIEN)]+ and thiols and thioethers
    Petrovic, BV
    Bugarcic, ZD
    JOURNAL OF COORDINATION CHEMISTRY, 2001, 53 (01) : 35 - 45
  • [42] Nitrosation of thiols and thioethers in the gas phase: A combined theoretical and experimental study
    Gerbaux, P. (pascal.gerbaux@umh.ac.be), 1600, Elsevier Inc. (15):
  • [43] Thiols, thioethers, and related compounds as sources of C-centred radicals
    Denes, Fabrice
    Schiesser, Carl H.
    Renaud, Philippe
    CHEMICAL SOCIETY REVIEWS, 2013, 42 (19) : 7900 - 7942
  • [44] SYNTHESIS OF ALLYL THIOETHERS
    GIESE, B
    MAZUMDAR, P
    CHEMISCHE BERICHTE-RECUEIL, 1981, 114 (08): : 2859 - 2865
  • [45] Asymmetric acetylenic thioethers in ruthenium cluster chemistry
    Alcalde, MI
    Delgado, E
    Donnadieu, B
    Hernández, E
    Martín, MP
    Zamora, F
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (03) : 552 - 556
  • [46] Asymmetric Thioethers as Building Blocks for Chiral Monolayers
    Jewell, April D.
    Tierney, Heather L.
    Zenasni, Oussama
    Lee, T. Randall
    Sykes, E. Charles H.
    TOPICS IN CATALYSIS, 2011, 54 (19-20) : 1357 - 1367
  • [47] Protodeboronation of Tertiary Boronic Esters: Asymmetric Synthesis of Tertiary Alkyl Stereogenic Centers
    Nave, Stefan
    Sonawane, Ravindra P.
    Elford, Tim G.
    Aggarwal, Varinder K.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (48) : 17096 - 17098
  • [48] Synthesis of Aryl Thioethers through the N-Chlorosuccinimide-Promoted Cross-Coupling Reaction of Thiols with Grignard Reagents
    Cheng, Jun-Hao
    Ramesh, Chintakunta
    Kao, Hsin-Lun
    Wang, Yu-Jen
    Chan, Chien-Ching
    Lee, Chin-Fa
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22): : 10369 - 10374
  • [49] Asymmetric Thioethers as Building Blocks for Chiral Monolayers
    April D. Jewell
    Heather L. Tierney
    Oussama Zenasni
    T. Randall Lee
    E. Charles H. Sykes
    Topics in Catalysis, 2011, 54 : 1357 - 1367
  • [50] Absolute Asymmetric Synthesis of Tertiary a-Amino Acids
    Thi Thoa Mai
    Branca, Mathieu
    Gori, Didier
    Guillot, Regis
    Kouklovsky, Cyrille
    Alezra, Valerie
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (20) : 4981 - 4984