Ultrafast Iron-Catalyzed Reduction of Functionalized Ketones: Highly Enantioselective Synthesis of Halohydrines, Oxaheterocycles, and Aminoalcohols

被引：35

作者：

Blasius, Clemens K. ^{[1
]}

Vasilenko, Vladislav ^{[1
]}

Gade, Lutz H. ^{[1
]}

机构：

[1] Heidelberg Univ, Anorgan Chem Inst, Neuenheimer Feld 270, D-69120 Heidelberg, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 32期

关键词：

amino alcohols; enantioselectivity; hydroboration; iron; ligand design; ASYMMETRIC TRANSFER HYDROGENATION; SECONDARY-AMINO KETONES; CHIRAL 1,2-AMINO ALCOHOLS; PINCER LIGANDS; DIASTEREOSELECTIVE SYNTHESIS; SUBSTITUTED ACETOPHENONES; ALKENE HYDROGENATION; PRACTICAL SYNTHESIS; ORGANIC-SYNTHESIS; AROMATIC KETONES;

D O I：

10.1002/anie.201806196

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A molecularly defined chiral boxmi iron alkyl complex catalyzes the hydroboration of various functionalized ketones and provides the corresponding chiral halohydrines, oxaheterocycles (oxiranes, oxetanes, tetrahydrofurans, and dioxanes) and amino alcohols with excellent enantioselectivities (up to >99%ee) and conversion efficiencies at low catalyst loadings (as low as 0.5mol%). Turnover frequencies of greater than 40000h(-1) at -30 degrees C highlight the activity of this earth-abundant metal catalyst which tolerates a large number of functional groups.

引用

页码：10231 / 10235

页数：5

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