Migratory Dynamic Kinetic Resolution of Carbocyclic Allylic Alcohols

被引:13
|
作者
Sapu, Chicco Manzuna [1 ]
Gorbe, Tamas [2 ]
Lihammar, Richard [2 ]
Backvall, Jan-E. [2 ]
Deska, Jan [1 ]
机构
[1] Univ Cologne, Dept Chem, D-50939 Cologne, Germany
[2] Stockholms Univ, Dept Organ Chem, S-10691 Stockholm, Sweden
基金
瑞典研究理事会;
关键词
TERTIARY ALCOHOLS; CATALYSIS; DESYMMETRIZATION; REARRANGEMENT;
D O I
10.1021/ol502979g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel migratory dynamic kinetic resolution based on the interplay between an enzyme acylation catalyst and a heterogeneous Bronsted acid as an isomerization/racemization catalyst gives rise to carbocyclic allylic esters with excellent stereoselectivity from readily available tertiary carbinols. An easy-to-use teabag setup combining resin-bound catalysts, a biphasic isooctanewater solvent system, and a highly lipophilic acyl donor efficiently suppresses side reactions and allows for the preparation of functionalized carbocyclic building blocks in high yields and optical purity.
引用
收藏
页码:5952 / 5955
页数:4
相关论文
共 50 条
  • [1] CHIRAL POISONING IN THE KINETIC RESOLUTION OF ALLYLIC ALCOHOLS
    FALLER, JW
    TOKUNAGA, M
    TETRAHEDRON LETTERS, 1993, 34 (46) : 7359 - 7362
  • [2] Iridium-catalysed asymmetric hydrogenation of allylic alcohols via dynamic kinetic resolution
    Liu, Jianguo
    Krajangsri, Suppachai
    Yang, Jianping
    Li, Jia-Qi
    Andersson, Pher G.
    NATURE CATALYSIS, 2018, 1 (06): : 438 - 443
  • [3] (S)-selective dynamic kinetic resolution of allylic alcohols by enzyme-metal bicatalysis
    Kim, Mahn-Joo
    Lee, Han Ki
    Park, Jaiwook
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2007, 28 (11): : 2096 - 2098
  • [4] Iridium-catalysed asymmetric hydrogenation of allylic alcohols via dynamic kinetic resolution
    Jianguo Liu
    Suppachai Krajangsri
    Jianping Yang
    Jia-Qi Li
    Pher G. Andersson
    Nature Catalysis, 2018, 1 : 438 - 443
  • [5] Chemoenzymatic dynamic kinetic resolution of allylic alcohols:: A highly enantioselective route to acyloin acetates
    Bogar, Krisztian
    Vidal, Pilar Hoyos
    Leon, Andres R. Alcantara
    Backvall, Jan-E.
    ORGANIC LETTERS, 2007, 9 (17) : 3401 - 3404
  • [6] Dynamic kinetic resolution of allylic alcohols mediated by ruthenium- and lipase-based catalysts
    Lee, D
    Huh, EA
    Kim, MJ
    Jung, HM
    Koh, JH
    Park, J
    ORGANIC LETTERS, 2000, 2 (15) : 2377 - 2379
  • [7] Asymmetric Hydrogenation of Racemic Allylic Alcohols via an Isomerization-Dynamic Kinetic Resolution Cascade
    Wang, Kun
    Niu, Saisai
    Guo, Xin
    Tang, Weijun
    Xue, Dong
    Xiao, Jianliang
    Sun, Huaming
    Wang, Chao
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (05): : 3804 - 3809
  • [8] Enzyme- and Ruthenium-Catalyzed Dynamic Kinetic Resolution of Functionalized Cyclic Allylic Alcohols
    Lihammar, Richard
    Millet, Renaud
    Backvall, Jan-E.
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (23): : 12114 - 12120
  • [9] Kinetic resolution of allylic alcohols using a chiral phosphine catalyst
    Vedejs, E
    MacKay, JA
    ORGANIC LETTERS, 2001, 3 (04) : 535 - 536
  • [10] Kinetic resolution of allylic alcohols promoted by electrophilic selenium reagents
    Santi, C
    Tiecco, M
    Testaferri, L
    Tomassini, C
    Marini, F
    Bagnoli, L
    Temperini, A
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2005, 180 (3-4) : 1071 - 1075