Lipase-Catalyzed Stereoselective Cross-Aldol Reaction Promoted by Water

被引:50
|
作者
Xie, Zong-Bo [1 ,2 ,3 ]
Wang, Na [1 ,2 ]
Zhou, Long-Hua [1 ,2 ]
Wan, Fang [1 ,2 ]
He, Ting [1 ,2 ]
Le, Zhang-Gao [3 ]
Yu, Xiao-Qi [1 ,2 ]
机构
[1] Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Chengdu 610064, Peoples R China
[2] Sichuan Univ, State Key Lab Oral Dis, Coll Chem, Chengdu 610064, Peoples R China
[3] E China Inst Technol, Sch Chem Biol & Mat Sci, Fuzhou 344000, Peoples R China
基金
中国国家自然科学基金;
关键词
aldol reaction; asymmetric catalysis; lipases; stereoselectivity; water chemistry; PORCINE PANCREATIC LIPASE; CARBON BOND FORMATION; ORGANIC MEDIA; BIOCATALYTIC PROMISCUITY; MARKOVNIKOV ADDITION; MICHAEL ADDITION; EPOXIDATION; ENZYMES;
D O I
10.1002/cctc.201200890
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
PPL, lipase from porcine pancreas, is first reported to catalyze direct asymmetric aldol reactions between aromatic aldehydes and cyclic ketones. More importantly, the catalytic activity of PPL was greatly promoted by a small quantity of water at 37 degrees C. A wide range of aromatic aldehydes reacted with cyclic ketones to provide the corresponding aldol products with high yields (up to 99%) and moderate to good stereoselectivity (up to 90%ee and 99:1 dr).
引用
收藏
页码:1935 / 1940
页数:6
相关论文
共 50 条
  • [21] Electron deficiency of aldehydes controls the pyrrolidine catalyzed direct cross-aldol reaction of aromatic/heterocyclic aldehydes and ketones in water
    Chimni, SS
    Mahajan, D
    TETRAHEDRON, 2005, 61 (21) : 5019 - 5025
  • [22] An approach towards (+)-allokainic acid via diphenylprolinol-catalyzed direct cross-aldol reaction
    Mhaldar, Shashank N.
    Tilve, Santosh G.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (26) : 5469 - 5474
  • [23] Asymmetric cross-aldol reaction of isatin and ketones catalyzed by crude earthworm extract as efficient biocatalyst
    Shams, Fatemeh
    Aliabad, Javad Mokhtari
    Rouhani, Morteza
    GREEN CHEMISTRY LETTERS AND REVIEWS, 2020, 13 (03) : 94 - 100
  • [24] DEVELOPMENT OF A NOVEL METHOD FOR WARFARIN SYNTHESIS VIA LIPASE-CATALYZED STEREOSELECTIVE MICHAEL REACTION
    Sano, Kaoru
    Saito, Shun-ichi
    Hirose, Yoshihiko
    Kohari, Yoshihito
    Nakano, Hiroto
    Seki, Chigusa
    Tokiwa, Michio
    Takeshita, Mitsuhiro
    Uwai, Koji
    HETEROCYCLES, 2013, 87 (06) : 1269 - 1278
  • [25] Subcritical Water Assisted Clean Cross-Aldol Reactions
    Wang, Pengyu
    Kobiro, Kazuya
    JOURNAL OF CHEMICAL ENGINEERING OF JAPAN, 2011, 44 (08) : 577 - 582
  • [26] An efficient green approach to aldol and cross-aldol condensations of ketones with aromatic aldehydes catalyzed by nanometasilica disulfuric acid in water
    A. Nakhaei
    A. Morsali
    A. Davoodnia
    Russian Journal of General Chemistry, 2017, 87 : 1073 - 1078
  • [27] An Efficient Green Approach to Aldol and Cross-Aldol Condensations of Ketones with Aromatic Aldehydes Catalyzed by Nanometasilica Disulfuric Acid in Water
    Nakhaei, A.
    Morsali, A.
    Davoodnia, A.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2017, 87 (05) : 1073 - 1078
  • [28] Engineering of lipase-catalyzed transesterification reaction media using water and diethylamine
    Szczesna-Antczak, Miroslawa
    Szelag, Jakub
    Stanczyk, Lukasz
    Borowska, Agnieszka
    Antczak, Tadeusz
    BIOCATALYSIS AND BIOTRANSFORMATION, 2016, 34 (06) : 253 - 264
  • [29] Diarylprolinol in an Asymmetric, Direct Cross-Aldol Reaction with Alkynyl Aldehydes
    Hayashi, Yujiro
    Kojima, Masahiro
    Yasui, Yusuke
    Kanda, Yuta
    Mukaiyama, Takasuke
    Shomura, Hiroki
    Nakamura, Daichi
    Ritmaleni
    Sato, Itaru
    CHEMCATCHEM, 2013, 5 (10) : 2887 - 2892
  • [30] Subcritical water assisted clean cross-aldol reactions
    School of Environmental Science and Engineering, Kochi University of Technology, 185 Miyanokuchi, Tosayamada-cho, Kami-shi, Kochi 782-8502, Japan
    J. Chem. Eng. Jpn., 8 (577-582):