Kinetic Resolution of α-Hydroxy-Substituted Oxime Ethers by Enantioselective Cu-H-Catalyzed Si-O Coupling

被引：28

作者：

Dong, Xichang ^{[1
]}

Kita, Yuji ^{[1
]}

Oestreich, Martin ^{[1
]}

机构：

[1] Tech Univ Berlin, Inst Chem, Str 17 Juni 115, D-10623 Berlin, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 33期

关键词：

asymmetric catalysis; copper; dehydrogenative coupling; kinetic resolution; silicon; STEREOSELECTIVE SILYLATION; ASYMMETRIC SILYLATION; ALCOHOLS; DERIVATIVES; SELECTIVITY; 1,2-DIOLS; HYDRIDE; SILANES;

D O I：

10.1002/anie.201802947

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A catalyst-controlled enantioselective alcohol silylation by Cu-H-catalyzed dehydrogenative Si-O coupling of hydroxy groups to an oxime ether and simple hydrosilanes is reported. The selectivity factors reached in this kinetic resolution are generally high (s approximate to 50), and these reactions thereby provide reliable access to highly enantioenriched-hydroxy-substituted oxime ethers. The synthetic usefulness of these compounds is also demonstrated.

引用

页码：10728 / 10731

页数：4

共 13 条

[1] Kinetic Resolution of Tertiary Propargylic Alcohols by Enantioselective Cu-H-Catalyzed Si-O Coupling
Seliger, Jan
Dong, Xichang
Oestreich, Martin
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (07) : 1970 - 1974
[2] Kinetic Resolution of BINOLs and Biphenols by Atroposelective, Cu-H-Catalyzed Si-O Coupling with Hydrosilanes
Boeser, Lisa A.
Oestreich, Martin
ORGANIC LETTERS, 2024, 26 (44) : 9531 - 9535
[3] Kinetic Resolution of Neopentylic Secondary Alcohols by Cu-H-Catalyzed Enantioselective Silylation with Hydrosilanes
Papadopulu, Zaneta
Oestreich, Martin
ORGANIC LETTERS, 2021, 23 (02) : 438 - 441
[4] Stereoselective Alcohol Silylation by Dehydrogenative Si-O Coupling: Scope, Limitations, and Mechanism of the Cu-H-Catalyzed Non-Enzymatic Kinetic Resolution with Silicon-Stereogenic Silanes
Rendler, Sebastian
Plefka, Oliver
Karatas, Betuel
Auer, Gertrud
Froehlich, Roland
Mueck-Lichtenfeld, Christian
Grimme, Stefan
Oestreich, Martin
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (36) : 11512 - 11528
[5] Catalytic enantioselective dehydrogenative Si-O coupling of oxime ether-functionalized alcohols
Weickgenannt, Andreas
Mohr, Jens
Oestreich, Martin
TETRAHEDRON, 2012, 68 (17) : 3468 - 3479
[6] Enantioselective Synthesis of Chiral Oxime Ethers: Desymmetrization and Dynamic Kinetic Resolution of Substituted Cyclohexanones
Nimmagadda, Sri Krishna
Mallojjala, Sharath Chandra
Woztas, Lukasz
Wheeler, Steven E.
Antilla, Jon C.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (09) : 2454 - 2458
[7] One out of Four: Kinetic Resolution of Stereoisomeric Mixtures of Secondary Alcohols with a Quaternary Carbon Atom in the β-Position by Cu-H-Catalyzed Enantioselective Silylation
Papadopulu, Zaneta
Kazeroonian, Novid
Irran, Elisabeth
Oestreich, Martin
ACS ORGANIC & INORGANIC AU, 2022, 2 (02): : 164 - 168
[8] Facile preparation of CF3-substituted carbinols with an azine donor and subsequent kinetic resolution through stereoselective Si-O coupling
Steves, Anne
Oestreich, Martin
ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (21) : 4464 - 4469
[9] One out of Four: Kinetic Resolution of Stereoisomeric Mixtures of Secondary Alcohols with a Quaternary Carbon Atom in the fl-Position by Cu-H-Catalyzed Enantioselective Silylation
Papadopulu, Zaneta
Kazeroonian, Novid
Irran, Elisabeth
Oestreich, Martin
ACS ORGANIC & INORGANIC AU, 2021, : 164 - 168
[10] Iridium-Catalyzed Site- and Enantioselective C(sp2)-H Borylation of Benzhydryl Ethers: Enantioselectivity Amplification by Kinetic Resolution Relay
Jing, Ke
Chen, Lili
Zhang, Panke
Xu, Senmiao
CHINESE JOURNAL OF CHEMISTRY, 2023, 41 (17) : 2119 - 2124

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