Chemo- and Stereoselective Iron-Catalyzed Hydrosilylation of Ketones

被引：97

作者：

Addis, Daniele ^{[1
]}

Shaikh, Nadim ^{[1
]}

Zhou, Shaolin ^{[1
]}

Das, Shoubhik ^{[1
]}

Junge, Kathrin ^{[1
]}

Beller, Matthius ^{[1
]}

机构：

[1] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2010年 / 5卷 / 07期

关键词：

asymmetric synthesis; enantioselectivity; hydrosilylation; iron; ketones; ASYMMETRIC TRANSFER HYDROGENATION; BIOMIMETIC TRANSFER HYDROGENATION; TRANSITION-METAL-COMPLEXES; ENANTIOSELECTIVE HYDROSILYLATION; CARBONYL-COMPOUNDS; REDUCTION; EFFICIENT; LIGANDS; POLYMETHYLHYDROSILOXANE; COORDINATION;

D O I：

10.1002/asia.201000064

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reduction of ketones with polymethylhydrosiloxane (PMHS) gives the corresponding alcohols in good to excellent yield applying iron-based catalyst systems. In the case of prochiral ketones, the use of Fe(OAc)(2)/(S,S)-Me-DuPhos leads to high enantioselectivity up to 99% ee. The reaction proceeds in the presence of several functional groups such as esters, halides as well as conjugated double bonds, with high chemoselectivity. The advantage of this protocol is that the reaction requires no activating agents or additives.

引用

页码：1687 / 1691

页数：5

共 95 条

[21]

CADE LH, 2004, ANGEW CHEM INT EDIT, V116, P1036

[22] Chemo- and enantioselective hydrosilylation of carbonyl and imino groups. An emphasis on non-traditional catalyst systems [J].

Carpentier, JF ;

Bette, V .

CURRENT ORGANIC CHEMISTRY, 2002, 6 (10) :913-936

[23] An efficient and chemoselective iron catalyst for the hydrogenation of ketones [J].

Casey, Charles P. ;

Guan, Hairong .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (18) :5816-+

[24] Cyclopentadienone Iron Alcohol Complexes: Synthesis, Reactivity, and Implications for the Mechanism of Iron-Catalyzed Hydrogenation of Aldehydes [J].

Casey, Charles P. ;

Guan, Hairong .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (07) :2499-2507

[25] Iron-catalysed carbon-heteroatom and heteroatom-heteroatom bond forming processes [J].

Correa, Arkaitz ;

Mancheno, Olga Garcia ;

Bolm, Carsten .

CHEMICAL SOCIETY REVIEWS, 2008, 37 (06) :1108-1117

[26] Coming of Age: Sustainable Iron-Catalyzed Cross-Coupling Reactions [J].

Czaplik, Waldemar Maximilian ;

Mayer, Matthias ;

Cvengros, Jan ;

Jacobi von Wangelin, Axel .

CHEMSUSCHEM, 2009, 2 (05) :396-417

[27] FeCl3-Catalyzed Reduction of Ketones and Aldehydes to Alkane Compounds [J].

Dal Zotto, Christophe ;

Virieux, David ;

Campagne, Jean-Marc .

SYNLETT, 2009, (02) :276-278

[28] Zinc-Catalyzed Reduction of Amides: Unprecedented Selectivity and Functional Group Tolerance [J].

Das, Shoubhik ;

Addis, Daniele ;

Zhou, Shaolin ;

Junge, Kathrin ;

Beller, Matthias .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (06) :1770-+

[29] Cationic copper(I) complexes as efficient precatalysts for the hydrosilylation of carbonyl compounds [J].

Díez-González, S ;

Scott, NM ;

Nolan, SP .

ORGANOMETALLICS, 2006, 25 (09) :2355-2358

[30] ASYMMETRIC CATALYTIC REDUCTION WITH TRANSITION-METAL COMPLEXES .2. ASYMMETRIC CATALYSIS BY A SUPPORTED CHIRAL RHODIUM COMPLEX [J].

DUMONT, W ;

POULIN, J ;

DANG, T ;

KAGAN, HB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (25) :8295-8299

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