(R)-1-Arylethanols from aryl iodides through a two-step one-pot enantioselective chemoenzymatic process

被引:9
|
作者
Cacchi, Sandro [3 ]
Cirilli, Roberto [2 ]
Fabrizi, Giancarlo [3 ]
Sgalla, Simona [2 ]
Macone, Alberto [1 ]
Bonamore, Alessandra [1 ]
Boffi, Alberto [1 ]
机构
[1] Univ Rome, Dipartimento Sci Biochim Sapienza, I-00185 Rome, Italy
[2] Ist Super Sanita, I-00161 Rome, Italy
[3] Univ Roma La Sapienza, Dipartimento Chim & Tecnol Farm, I-00185 Rome, Italy
关键词
Asimmetric synthesis; Palladium catalysis; Alcohol dehydrogenase; ASYMMETRIC TRANSFER HYDROGENATION; DYNAMIC KINETIC RESOLUTION; PROCHIRAL KETONES; COMPLEXES; REDUCTION; CATALYST; MECHANISM; ALCOHOLS; LIGANDS;
D O I
10.1016/j.molcatb.2009.06.009
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
(R)-1-Arylethanols have been prepared in high to excellent overall yields through a two-step one-pot process that involves the palladium-catalyzed conversion of aryl iodides into the corresponding acetophenones, in the presence of acetic anhydride. EtN(i-Pr)(2), LiCl, and Pd-2(dba)(3) followed by an enantioselective reduction step catalyzed by the alcohol dehydrogenase enzyme from Lactobacillus brevis. (C) 2009 Elsevier B.V. All rights reserved.
引用
收藏
页码:184 / 187
页数:4
相关论文
共 50 条
  • [1] Copper-Catalyzed One-Pot Synthesis of α-Ketoamides from 1-Arylethanols
    Sharma, Nidhi
    Kotha, Surya Srinivas
    Lahiri, Nabajit
    Sekar, Govindasamy
    SYNTHESIS-STUTTGART, 2015, 47 (05): : 726 - 736
  • [2] One-Pot Two-Step Chemoenzymatic Cascade for the Synthesis of a Bis-benzofuran Derivative
    Mertens, M. A. Stephanie
    Thomas, Fabian
    Noeth, Maximilian
    Moegling, Julian
    El-Awaad, Islam
    Sauer, Daniel F.
    Dhoke, Gaurao V.
    Xu, Wenjing
    Pich, Andrij
    Herres-Pawlis, Sonja
    Schwaneberg, Ulrich
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (37) : 6341 - 6346
  • [3] One-pot two-step stannylation/Stille homocoupling of aryl bromides and iodides under solvent-free conditions
    Gribanov, Pavel S.
    Golenko, Yulia D.
    Topchiy, Maxim A.
    Philippova, Anna N.
    Kirilenko, Nikita Yu.
    Krivoshchapov, Nikolai V.
    Sterligov, Grigorii K.
    Asachenko, Andrey F.
    Bermeshev, Maxim V.
    Nechaev, Mikhail S.
    MENDELEEV COMMUNICATIONS, 2018, 28 (03) : 323 - 325
  • [4] One-pot synthesis of 1,3-diaryl but-1-enes from 1-arylethanols over Snβ zeolite
    Mameda, Naresh
    Gajula, Krishna Sai
    Peraka, Swamy
    Kodumuri, Srujana
    Chevella, Durgaiah
    Banothu, Rammurthy
    Amrutham, Vasu
    Nama, Narender
    CATALYSIS COMMUNICATIONS, 2017, 90 : 95 - 99
  • [5] One-pot two-step chemoenzymatic deracemization of allylic alcohols using laccases and alcohol dehydrogenases
    Albarran-Velo, Jesus
    Gotor-Fernandez, Vicente
    Lavandera, Ivan
    MOLECULAR CATALYSIS, 2020, 493 (493)
  • [6] One-Pot Chemoenzymatic Cascade for the Enantioselective C(1)-Allylation of Tetrahydroisoquinolines
    Sangster, Jack J.
    Ruscoe, Rebecca E.
    Cosgrove, Sebastian C.
    Mangas-Sanchez, Juan
    Turner, Nicholas J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (08) : 4431 - 4437
  • [7] A general two-step one-pot synthesis process of ynones from α-keto acids and 1-iodoalkynes
    Zeng, Xiaobao
    Liu, Chulong
    Yang, Weiguang
    Wang, Xingyong
    Wang, Xinyan
    Hu, Yuefei
    CHEMICAL COMMUNICATIONS, 2018, 54 (68) : 9517 - 9520
  • [8] Straightforward Assembly of Phenylimidazoquinoxalines via a One-Pot Two-Step MCR Process
    De Moliner, Fabio
    Hulme, Christopher
    ORGANIC LETTERS, 2012, 14 (05) : 1354 - 1357
  • [9] A convenient two-step one-pot synthesis of phosphonamidates
    Mlodnosky, KL
    Holmes, HM
    Lam, VQ
    Berkman, CE
    TETRAHEDRON LETTERS, 1997, 38 (51) : 8803 - 8806
  • [10] One-Pot, Two-Step Cascade Synthesis of Quinazolinotriazolobenzodiazepines
    Guggenheim, Kathryn G.
    Toru, Hannah
    Kurth, Mark J.
    ORGANIC LETTERS, 2012, 14 (14) : 3732 - 3735