Oxazolidinones as chiral auxiliaries in asymmetric aldol reactions applied to total synthesis

被引:163
|
作者
Heravi, Majid M. [1 ]
Zadsirjan, Vahideh [1 ]
机构
[1] Alzahra Univ, Sch Sci, Dept Chem, Tehran, Iran
关键词
STEREOSELECTIVE TOTAL-SYNTHESIS; CYTOTOXIC 35-MEMBERED CYCLODEPSIPEPTIDES; CYANOBACTERIUM LYNGBYA-MAJUSCULA; ICHTHYOTOXIC CYCLIC LIPOPEPTIDE; DINOFLAGELLATE AMPHIDINIUM SP; ALDER CYCLOADDITION REACTIONS; DIARRHETIC SHELLFISH TOXINS; SPONGE DYSIDEA-ARENARIA; MICROSCLERODERMINS F-I; FORMAL TOTAL SYNTHESIS;
D O I
10.1016/j.tetasy.2013.08.011
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Asymmetric aldol reactions of oxazolidinones as chiral auxiliaries have been achieved and attracted significant consideration as one of the most powerful synthetic tools for the carbon-carbon bond-forming reactions. The methodology has been highly successful in the stereoselective construction of a number of natural products, antibiotics, and other medicinally important compounds. The present review is focused on the utility and versatility of oxazolidinones (Evans chiral auxiliaries) in the asymmetric aldol condensations for the total synthesis of natural products and complex targets. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1149 / 1188
页数:40
相关论文
共 50 条
  • [1] Oxazolidinones as chiral auxiliaries in asymmetric aldol reaction applied to natural products total synthesis
    Nazari, Azadeh
    Heravi, Majid M.
    Zadsirjan, Vahideh
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2021, 932
  • [2] Applications of oxazolidinones as chiral auxiliaries in the asymmetric alkylation reaction applied to total synthesis
    Heravi, Majid M.
    Zadsirjan, Vahideh
    Farajpour, Behnaz
    RSC ADVANCES, 2016, 6 (36) : 30498 - 30551
  • [3] Applications of oxazolidinones as chiral auxiliaries in the asymmetric alkylation reaction applied to total synthesis
    Heravi M.M.
    Zadsirjan V.
    Farajpour B.
    Heravi, Majid M. (mmh1331@yahoo.com), 1600, Royal Society of Chemistry (06): : 30498 - 30551
  • [4] Asymmetric synthesis of lignans using oxazolidinones as chiral auxiliaries
    Charlton, James L.
    Chee, Gaik-Lean
    1997, NRC Res Press, Ottawa, Canada (75)
  • [5] Asymmetric synthesis of lignans using oxazolidinones as chiral auxiliaries
    Charlton, JL
    Chee, GL
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1997, 75 (08): : 1076 - 1083
  • [6] Oxazolidinones as Chiral Auxiliaries in the Asymmetric 1,4-Conjugate Addition Reaction Applied to the Total Synthesis of Natural Products: A Supplemental Mini-Review
    Zadsirjan, Vahideh
    Heravi, Majid M.
    CURRENT ORGANIC SYNTHESIS, 2018, 15 (01) : 3 - 20
  • [7] Oxazinanones as chiral auxiliaries: synthesis and evaluation in enolate alkylations and aldol reactions
    Davies, Stephen G.
    Garner, A. Christopher
    Roberts, Paul M.
    Smith, Andrew D.
    Sweet, Miles J.
    Thomson, James E.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (14) : 2753 - 2768
  • [8] Chiral oxazolidinones in asymmetric synthesis
    Ager, DJ
    Prakash, I
    Schaad, DR
    ALDRICHIMICA ACTA, 1997, 30 (01) : 3 - 12
  • [9] REACTIVE POLYMERS AS CHIRAL AUXILIARIES IN ASYMMETRIC REACTIONS
    FRECHET, JMJ
    LECAVALIER, P
    BALD, E
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1985, 189 (APR-): : 76 - ORGN
  • [10] Chiral Thiazolidine based Organocatalysts: Synthesis and Application in Asymmetric Aldol Reactions
    Felix, Ana Rita G.
    Simoes, Pedro R. D.
    Sousa, Francisco J. P. M.
    Silva Serra, M. Elisa
    Murtinho, Dina
    LETTERS IN ORGANIC CHEMISTRY, 2020, 17 (05) : 372 - 380