Boronic Esters in Asymmetric Synthesis

被引：236
|
作者：
Matteson, Donald S. [1 ]
机构：
[1] Washington State Univ, Pullman, WA 99164 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 20期
基金：
美国国家卫生研究院;
关键词：
DIRECTED CHIRAL SYNTHESIS; TRANSITION-STATE ANALOG; X-RAY-STRUCTURE; SEX-PHEROMONE; DRUGSTORE BEETLE; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; INSECT PHEROMONES; AMINO-ACIDS; HOMOLOGATION;
D O I：
10.1021/jo4013942
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The author's work on (alpha-haloalkyl)boronic esters as reagents for asymmetric synthesis is reviewed. Diastereomeric ratios exceeding 1000 can be achieved with this chemistry, and ratios around 100 are commonplace. The method allows sequential installation of a series of stereocenters and tolerates a wide variety of suitably protected functional substituents. (alpha-Amidoalkyl)boronic acids include biochemically significant serine protease inhibitors, one of which is the clinically successful proteasome inhibitor bortezomib, used for treatment of multiple myeloma and mantle cell lymphoma.
引用
收藏
页码：10009 / 10023
页数：15
相关论文
共 50 条
  • [21] The Synthesis of trans-Perhydroindolic Acids and their Application in Asymmetric Domino Reactions of Aldehyde Esters with β,γ-Unsaturated α-Keto Esters
    Shen, Jiefeng
    Liu, Delong
    An, Qianjin
    Liu, Yangang
    Zhang, Wanbin
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (17) : 3311 - 3325
  • [22] Highly Enantiospecific Borylation for Chiral α-Amino Tertiary Boronic Esters
    Qi, Qingqing
    Yang, Xuena
    Fu, Xiaoping
    Xu, Shiqing
    Negishi, Ei-ichi
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (46) : 15138 - 15142
  • [23] Stereodivergent Olefination of Enantioenriched Boronic Esters
    Armstrong, Roly J.
    Garcia-Ruiz, Cristina
    Myers, Eddie L.
    Aggarwal, Varinder K.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (03) : 786 - 790
  • [24] Synthesis of Highly Enantioenriched C-Tertiary Amines From Boronic Esters: Application to the Synthesis of Igmesine
    Bagutski, Viktor
    Elford, Tim G.
    Aggarwal, Varinder K.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (05) : 1080 - 1083
  • [25] Organocatalytic Asymmetric Synthesis of β-Aryl-β-isocyano Esters
    Morana, Fabio
    Basso, Andrea
    Bella, Marco
    Riva, Renata
    Banfi, Luca
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (11-12) : 2199 - 2210
  • [26] Strategies for the asymmetric synthesis of H-phosphinate esters
    Bravo-Altamirano, Karla
    Coudray, Laetitia
    Deal, Eric L.
    Montchamp, Jean-Luc
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (24) : 5541 - 5551
  • [27] Homologation and Alkylation of Boronic Esters and Boranes by 1,2-Metallate Rearrangement of Boron Ate Complexes
    Thomas, Stephen P.
    French, Rosalind M.
    Jheengut, Vishal
    Aggarwal, Varinder K.
    CHEMICAL RECORD, 2009, 9 (01): : 24 - 39
  • [28] Glycosylidene-carbene-mediated homologation of boronic esters for the synthesis of boro-ketosides
    Zhu, Qibin
    Tian, Xinyu
    He, Gang
    CHEM CATALYSIS, 2024, 4 (04):
  • [29] Asymmetric Synthesis of α-Allenylglycines
    Bucuroaia, Carmen
    Groth, Ulrich
    Huhn, Thomas
    Klinge, Michael
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (21) : 3605 - 3612
  • [30] Visible-Light-Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ-Amino Boronic Esters
    Noble, Adam
    Mega, Riccardo S.
    Pflaesterer, Daniel
    Myers, Eddie L.
    Aggarwal, Varinder K.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (08) : 2155 - 2159
12345