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

页码：2487 / 2489

页数：3

共 50 条

[31] Kinetic resolution of racemic secondary aliphatic allylic alcohols in lipase-catalyzed transesterification
Chojnacka, Anna
Obara, Robert
Wawrzenczyk, Czeslaw
TETRAHEDRON-ASYMMETRY, 2007, 18 (01) : 101 - 107
[32] Highly efficient dynamic kinetic resolution of secondary aromatic alcohols at low temperature using a low-cost sulfonated sepiolite as racemization catalyst
Wu, Jian-Ping
Meng, Xiao
Wang, Liang
Xu, Gang
Yang, Li-Rong
TETRAHEDRON LETTERS, 2014, 55 (37) : 5129 - 5132
[33] AN AIR-STABLE CATALYST SYSTEM FOR THE CONVERSION OF ESTERS TO ALCOHOLS (VOL 57, PG 3751, 1992)
BERK, SC
BUCHWALD, SL
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (11): : 3221 - 3221
[34] Recyclable and Scalable Chemoenzymatic Dynamic Kinetic Resolution of Secondary Alcohols Using Rotating Bed Reactors for Catalyst Compartmentalization
de Almeida, Laiza A.
Lofgren, Erik
Milagre, Cintia D. F.
Milagre, Humberto M. S.
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2024, 63 (25) : 11009 - 11017
[35] Chemoenzymatic synthesis of macrocycles via dynamic kinetic resolution of secondary alcohols
Guerrero-Morales, Javier
Scaglia, Marie
Fauran, Edouard
Lepage, Guillaume
Collins, Shawn K.
NATURE SYNTHESIS, 2024, 3 (10): : 1275 - 1282
[36] Heterogeneous Catalysts for Racemization and Dynamic Kinetic Resolution of Amines and Secondary Alcohols
Parvulescu, Andrei
Janssens, Joost
Vanderleyden, Jozef
De Vos, Dirk
TOPICS IN CATALYSIS, 2010, 53 (13-14) : 931 - 941
[37] Heterogeneous Catalysts for Racemization and Dynamic Kinetic Resolution of Amines and Secondary Alcohols
Andrei Parvulescu
Joost Janssens
Jozef Vanderleyden
Dirk De Vos
Topics in Catalysis, 2010, 53 : 931 - 941
[38] Bienzymatic Dynamic Kinetic Resolution of Secondary Alcohols by Esterification/Racemization in Water
Rudzka, Aleksandra
Reiter, Tamara
Kroutil, Wolfgang
Borowiecki, Pawel
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (08)
[39] Lipase/aluminum-catalyzed dynamic kinetic resolution of secondary alcohols
Berkessel, Albrecht
Sebastian-Ibarz, M. Luisa
Mueller, Thomas N.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (39) : 6567 - 6570
[40] A Dinuclear Dysprosium Complex as an Air-Stable and Recyclable Catalyst: Applications in the Deacetylation of Carbohydrate, Aliphatic, and Aromatic Molecules
Chiu, Ting-Yu
Chin, Wei
Guo, Jiun-Rung
Liang, Chien-Fu
Lin, Po-Heng
CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (05) : 627 - 633

← 1 2 3 4 5 →