New air-stable iron catalyst for efficient dynamic kinetic resolution of secondary benzylic and aliphatic alcohols

被引：20
|
作者：
Yang, Qiong [1 ]
Zhang, Na [1 ]
Liu, Mingke [1 ]
Zhou, Shaolin [1 ]
机构：
[1] Cent China Normal Univ, Coll Chem, CCNU uOttawa Joint Res Ctr, Key Lab Pesticide & Chem Biol,Minist Educ, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China
来源：
TETRAHEDRON LETTERS | 2017年 / 58卷 / 25期
关键词：
Dynamic kinetic resolution; Aliphatic alcohol; Benzylic alcohol; Iron catalysis; Racemization; CYCLOPENTADIENONE CATALYST; RACEMIZATION CATALYSTS; ENZYMATIC RESOLUTION; AMBIENT-TEMPERATURE; AROMATIC ALCOHOLS; COMPLEXES; AMINES; HYDROGENATION; RUTHENIUM; LIPASE;
D O I：
10.1016/j.tetlet.2017.05.038
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We herein report a catalyst system for the dynamic kinetic resolution of secondary alcohols by combining the enzymatic resolution with an iron-catalyzed racemization. A new air-stable tricarbonyl (cyclopentadienone)iron complex is identified as the active racemization catalyst for this transformation without any additive. Various substrates including benzylic, heteroaromatic, aliphatic alcohols can be used and afford the corresponding esters in good yields and with excellent enantioselectivities. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2487 / 2489
页数：3
相关论文
共 50 条
  • [1] Air-stable racemization catalyst for dynamic kinetic resolution of secondary alcohols at room temperature
    Kim, N
    Ko, SB
    Kwon, MS
    Kim, MJ
    Park, J
    ORGANIC LETTERS, 2005, 7 (20) : 4523 - 4526
  • [2] Air-stable racemization catalysts for the dynamic kinetic resolution of secondary alcohols
    Ko, Soo-Byung
    Baburaj, Baskar
    Kim, Mahn-Joo
    Park, Jaiwook
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (18): : 6860 - 6864
  • [3] Chemoenzymatic Dynamic Kinetic Resolution of Secondary Alcohols Using an Air- and Moisture-Stable Iron Racemization Catalyst
    Gustafson, Karl P. J.
    Gudmundsson, Arnar
    Lewis, Kayla
    Backvall, Jan-E.
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (05) : 1048 - 1051
  • [4] Air-stable iron catalyst for the Oppenauer-type oxidation of alcohols
    Moyer, Sara A.
    Funk, Timothy W.
    TETRAHEDRON LETTERS, 2010, 51 (41) : 5430 - 5433
  • [5] Photoactivated Racemization Catalyst for Dynamic Kinetic Resolution of Secondary Alcohols
    Do, Youngshil
    Hwang, In-Chul
    Kim, Mahn-Joo
    Park, Jaiwook
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (16): : 5740 - 5742
  • [6] Dynamic kinetic resolution of secondary aromatic alcohols with new efficient acyl donors
    Xu, Gang
    Chen, Yongjun
    Wu, Jianping
    Cheng, Yongmei
    Yang, Lirong
    TETRAHEDRON-ASYMMETRY, 2011, 22 (13) : 1373 - 1378
  • [7] AN AIR-STABLE CATALYST SYSTEM FOR THE CONVERSION OF ESTERS TO ALCOHOLS
    BERK, SC
    BUCHWALD, SL
    JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14): : 3751 - 3753
  • [8] A highly enantioselective phosphabicyclooctane catalyst for the kinetic resolution of benzylic alcohols
    Vedejs, E
    Daugulis, O
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (14) : 4166 - 4173
  • [9] A highly enantioselective phosphabicyclooctane catalyst for the kinetic resolution of benzylic alcohols
    Vedejs, Edwin
    Daugulis, Olafs
    Journal of the American Chemical Society, 2003, 125 (14): : 4166 - 4173
  • [10] Dicarbonylchloro(pentabenzylcyclopentadienyl)ruthenium as Racemization Catalyst in the Dynamic Kinetic Resolution of Secondary Alcohols
    Mavrynsky, Denys
    Paivio, Mari
    Lundell, Katri
    Sillanpaa, Reijo
    Kanerva, Liisa T.
    Leino, Reko
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (09) : 1317 - 1320
12345