Regioselective Functionalization of the Oxazole Scaffold Using TMP-Bases of Mg and Zn

被引：45
作者：
Haas, Diana [1 ]
Mosrin, Marc [2 ]
Knochel, Paul [1 ]
机构：
[1] Univ Munich, Dept Chem, D-81377 Munich, Germany
[2] Bayer CropSci AG, D-65926 Frankfurt, Germany
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 24期
基金：
欧洲研究理事会;
关键词：
CENTER-DOT-LICL; CROSS-COUPLING REACTION; ALKENYLMAGNESIUM REAGENTS; GENERAL METHODOLOGY; PALLADIUM; ARYL; DERIVATIVES; METALATION; MAGNESIATION; ZINCATION;
D O I：
10.1021/ol403019c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A general method for the synthesis of 2,4,5-trisubstituted oxazoles has been developed. Starting from commercially available oxazole, successive metalations using TMPMgCl center dot LiCl or TMPZnCl center dot LiCl led to the corresponding magnesiated or zincated species which were stable toward ring fragmentation. Furthermore, they readily reacted with various electrophiles, such as aryl and allylic halides, acid chlorides, TMSCl, and TMS-CN, providing highly functionalized oxazoles.
引用
收藏
页码：6162 / 6165
页数：4
相关论文
共 74 条
  • [61] CONVENIENT SYNTHESIS OF ACETYLENES - CATALYTIC SUBSTITUTIONS OF ACETYLENIC HYDROGEN WITH BROMOALKENES, IODOARENES, AND BROMOPYRIDINES
    SONOGASHIRA, K
    TOHDA, Y
    HAGIHARA, N
    [J]. TETRAHEDRON LETTERS, 1975, (50) : 4467 - 4470
  • [62] Highly Regioselective Palladium-Catalyzed Direct Arylation of Oxazole at C-2 or C-5 with Aryl Bromides, Chlorides, and Triflates
    Strotman, Neil A.
    Chobanian, Harry R.
    Guo, Yan
    He, Jiafang
    Wilson, Jonathan E.
    [J]. ORGANIC LETTERS, 2010, 12 (16) : 3578 - 3581
  • [63] Mechanism Selection for Regiocontrol in Base-Assisted, Palladium-Catalysed Direct C-H Coupling with Halides: First Approach for Oxazole- and Thiazole-4-Carboxylates
    Theveau, Laure
    Verrier, Cecile
    Lassalas, Pierrik
    Martin, Thibaut
    Dupas, Georges
    Querolle, Olivier
    Van Hijfte, Luc
    Marsais, Francis
    Hoarau, Christophe
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (51) : 14450 - 14463
  • [64] FLUORESCENCE AND CHEMILUMINESCENCE DETECTION OF OXAZOLE-LABELED AMINES AND THIOLS
    TOYOOKA, T
    CHOKSHI, HP
    GIVENS, RS
    CARLSON, RG
    LUNTE, SM
    KUWANA, T
    [J]. BIOMEDICAL CHROMATOGRAPHY, 1993, 7 (04) : 208 - 216
  • [65] CHEMISTRY OF OXAZOLES
    TURCHI, IJ
    DEWAR, MJS
    [J]. CHEMICAL REVIEWS, 1975, 75 (04) : 389 - 437
  • [66] New Preparation of TMPZnCl LiCl by Zn Insertion into TMPCl. Application to the Functionalization of Dibromodiazines
    Unsinn, Andreas
    Ford, Mark J.
    Knochel, Paul
    [J]. ORGANIC LETTERS, 2013, 15 (05) : 1128 - 1131
  • [67] A method for iodination of oxazoles at C-4 via 2-lithiooxazoles
    Vedejs, E
    Luchetta, LM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) : 1011 - 1014
  • [68] Metalation of oxazole-borane complexes: A practical solution to the problem of electrocyclic ring opening of 2-lithiooxazoles
    Vedejs, E
    Monahan, SD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) : 5192 - 5193
  • [69] Recent advances in direct C-H arylation: Methodology, selectivity and mechanism in oxazole series
    Verrier, Cecile
    Lassalas, Pierrik
    Theveau, Laure
    Queguiner, Guy
    Trecourt, Francois
    Marsais, Francis
    Hoarau, Christophe
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 : 1584 - 1601
  • [70] WITTIG-HORNER REACTION IN HETEROGENEOUS MEDIA .1. AN EASY SYNTHESIS OF ETHYL ALPHA-HYDROXYMETHYLACRYLATE AND ETHYL ALPHA-HALOMETHYLACRYLATES USING FORMALDEHYDE IN WATER
    VILLIERAS, J
    RAMBAUD, M
    [J]. SYNTHESIS-STUTTGART, 1982, (11): : 924 - 926
12345678