Arylboronic Acid-Catalyzed Racemization of Secondary and Tertiary Alcohols

被引：3
|
作者：
Boyce, Gregory R. [1 ,2 ]
Musolino, Stefania F. [1 ]
Yang, Jianing [1 ]
Smith, Andrew D. [1 ]
Taylor, James E. [3 ]
机构：
[1] Univ St Andrews, Sch Chem, EaStCHEM, St Andrews KY16 9ST, Fife, Scotland
[2] Florida Gulf Coast Univ, Dept Chem & Phys, Ft Myers, FL 33965 USA
[3] Univ Bath, Dept Chem, Bath, Avon BA2 7AY, England
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 19期
基金：
英国工程与自然科学研究理事会;
关键词：
DYNAMIC KINETIC RESOLUTION; AROMATIC ALCOHOLS; LOW-COST; EFFICIENT; ACTIVATION; MECHANISM; MILD;
D O I：
10.1021/acs.joc.2c01602
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The use of 2-carboxyphenylboronic acid (5 mol %) and oxalic acid (10 mol %) with 2-butanone as a solvent for the racemization of a range of enantiomerically pure secondary and tertiary alcohols is demonstrated. The process is postulated to proceed via reversible Br??nsted acid-catalyzed C???O bond cleavage through an achiral carbocation intermediate. <comment>Superscript/Subscript Available</comment
引用
收藏
页码：13367 / 13374
页数：8
相关论文
共 50 条
  • [21] ACID-CATALYZED DEHYDRATION OF ALCOHOLS IN SUPERCRITICAL WATER
    RAMAYYA, S
    BRITTAIN, A
    DEALMEIDA, C
    MOK, W
    ANTAL, MJ
    FUEL, 1987, 66 (10) : 1364 - 1371
  • [22] Racemization of secondary alcohols catalyzed by ruthenium: application to chemoenzymatic dynamic resolution
    Merabet-Khelassi, Mounia
    Vriamont, Nicolas
    Aribi-Zouioueche, Louisa
    Riant, Olivier
    TETRAHEDRON-ASYMMETRY, 2011, 22 (18-19) : 1790 - 1796
  • [23] ACID-CATALYZED OXIDATION OF ALCOHOLS BY M-CHLOROPERBENZOIC ACID
    CELLA, JA
    MCGRATH, JP
    REGEN, SL
    TETRAHEDRON LETTERS, 1975, (47) : 4115 - 4118
  • [24] ACID-CATALYZED HYDROLYSIS OF METHOXYMETHYL PHENYL SULFOXIDE WITHOUT CONCOMITANT RACEMIZATION
    OKUYAMA, T
    TOYODA, M
    FUENO, T
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (05) : 1316 - 1321
  • [25] Lewis acid-catalyzed direct amination of benzhydryl alcohols
    Terrasson, Vincent
    Marque, Sylvain
    Georgy, Marie
    Campagne, Jean-Marc
    Prim, Damien
    ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (15) : 2063 - 2067
  • [26] A general Bronsted acid-catalyzed allylation of benzhydryl alcohols
    Orizu, Ifedi
    Solshan, Yuri
    TETRAHEDRON LETTERS, 2016, 57 (51) : 5798 - 5800
  • [27] Acid-catalyzed hydrolysis of alcohols and their β-D-glucopyranosides
    Skouroumounis, GK
    Sefton, MA
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2000, 48 (06) : 2033 - 2039
  • [28] BIMOLECULAR KINETICS DURING ACID-CATALYZED DEHYDRATION OF ALCOHOLS
    HO, I
    SMITH, JG
    TETRAHEDRON LETTERS, 1970, (41) : 3535 - &
  • [29] LEWIS ACID-CATALYZED BORONO-MINISCI REACTIONS OF ARYLBORONIC ACIDS AND HETEROCYCLES
    Biaco, Joyce L.
    Jones, Savannah L.
    Barker, Timothy J.
    HETEROCYCLES, 2016, 92 (09) : 1687 - 1697
  • [30] Mechanism of arylboronic acid-catalyzed amidation reaction between carboxylic acids and amines
    Wang, Chen
    Yu, Hai-Zhu
    Fu, Yao
    Guo, Qing-Xiang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (13) : 2140 - 2146
12345