Enantioselective Isomerization of Primary Allylic Alcohols into Chiral Aldehydes with the tol-binap/dbapen/Ruthenium(II) Catalyst

被引：62
作者：
Arai, Noriyoshi [1 ,2 ]
Sato, Keisuke [1 ,2 ]
Azuma, Keita [1 ,2 ]
Ohkuma, Takeshi [1 ,2 ]
机构：
[1] Hokkaido Univ, Div Chem Proc Engn, Sapporo, Hokkaido 0608628, Japan
[2] Hokkaido Univ, Fac Engn, Frontier Chem Ctr, Sapporo, Hokkaido 0608628, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 29期
基金：
日本学术振兴会;
关键词：
aldehydes; allylic alcohols; asymmetric catalysis; isomerization; ruthenium; RUTHENIUM-CYCLOPENTADIENYL COMPLEXES; ASYMMETRIC ISOMERIZATION; REDOX ISOMERIZATION; COORDINATION CHEMISTRY; STEREOSELECTIVE HYDROGENATION; CARBONYL-COMPOUNDS; LIGANDS; KETONES; REDUCTION; SCOPE;
D O I：
10.1002/anie.201303423
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Efficient isomerization: The title reaction was catalyzed by the [RuCl 2{(S)-tol-binap}{(R)-dbapen}]/KOH system in ethanol at 25°C (see scheme). A series of E- and Z-configured aromatic and aliphatic allylic alcohols, including a simple primary alkyl-substituted compound (E)-3-methyl-2-hepten-1-ol, were transformed into the chiral aldehydes with at least 99 % ee. dbapen=2-dibutylamino-1-phenylethylamine, tol-binap=2,2′- bis(di-4-tolylphosphanyl)-1,1′-binaphthyl. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：7500 / 7504
页数：5
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