Nickel-Catalyzed Reductive Allylation of Aldehydes with Allyl Acetates

被引：6

作者：

Suzuki, Hiroyuki ^{[1
]}

Yamaguchi, Eiji ^{[1
]}

Itoh, Akichika ^{[1
]}

机构：

[1] Gifu Pharmaceut Univ, Lab Pharmaceut Synthet Chem, 1-25-4 Daigaku Nishi, Gifu 5011196, Japan

来源：

SYNTHESIS-STUTTGART | 2021年 / 53卷 / 08期

关键词：

reductive allylation; nickel complex; allyl acetate; carbonyl addition; transition-metal catalysis; CARBONYL-COMPOUNDS; ENANTIOSELECTIVE SYNTHESIS; NUCLEOPHILIC ALLYLATION; ALKYL BROMIDES; ACTIVATION; ALCOHOL; REAGENT; HALIDES; DESIGN; IMINES;

D O I：

10.1055/s-0040-1705961

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Carbonyl allylation reactions constitute an important step in the formation of carbon-carbon reactions, and involve various related reactions that chiefly use allylmetal reagents. This report presents a nickel-catalyzed carbonyl allylation reaction using allyl acetate, which produces homoallyl alcohols in moderate to good yields, as an efficient methodology under reductive coupling conditions.

引用

页码：1489 / 1494

页数：6

共 68 条

[1] Progress and developments in the turbo Grignard reagent i-PrMgCl•LiCl: a ten-year journey [J].

Bao, Robert Li-Yuan ;

Zhao, Rong ;

Shi, Lei .

CHEMICAL COMMUNICATIONS, 2015, 51 (32) :6884-6900

[2] Enantioselective Iridium-Catalyzed Allylation of Acetylenic Ketones via 2-Propanol-Mediated Reductive Coupling of Allyl Acetate: C14-C23 of Pladienolide D [J].

Brito, Gilmar A. ;

Jung, Woo-Ok ;

Yoo, Minjin ;

Krische, Michael J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (52) :18803-18807

[3] Total Synthesis of Clavosolide A via Asymmetric Alcohol-Mediated Carbonyl Allylation: Beyond Protecting Groups or Chiral Auxiliaries in Polyketide Construction [J].

Cabrera, James M. ;

Krische, Michael J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (31) :10718-10722

[4] Selection between Diastereomeric Kinetic vs Thermodynamic Carbonyl Binding Modes Enables Enantioselective Iridium-Catalyzed anti-(α-Aryl)allylation of Aqueous Fluoral Hydrate and Difluoroacetaldehyde Ethyl Hemiacetal [J].

Cabrera, James M. ;

Tauber, Johannes ;

Zhang, Wandi ;

Xiang, Ming ;

Krische, Michael J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (30) :9392-9395

[5] Enantioselective Iridium-Catalyzed Phthalide Formation through Internal Redox Allylation of Phthalaldehydes [J].

Cabrera, James M. ;

Tauber, Johannes ;

Krische, Michael J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (05) :1390-1393

[6] Nickel-Catalyzed Allylation of a-Amido Sulfones To Form Protected Homoallylic Amines [J].

Caputo, Jill A. ;

Naodovic, Marina ;

Weix, Daniel J. .

SYNLETT, 2015, 26 (03) :323-326

[7] 15 YEARS OF REDUCTIVE COUPLING - WHAT HAVE WE LEARNED [J].

CARNAHAN, EM ;

PROTASIEWICZ, JD ;

LIPPARD, SJ .

ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (03) :90-97

[8] Enantioselective Synthesis of α-exo-Methylene γ-Butyrolactones via Chromium Catalysis [J].

Chen, Weiqiang ;

Yang, Qin ;

Zhou, Tian ;

Tian, Qingshan ;

Zhang, Guozhu .

ORGANIC LETTERS, 2015, 17 (21) :5236-5239

[9] Polystyrene-Supported TRIP: A Highly Recyclable Catalyst for Batch and Flow Enantioselective Allylation of Aldehydes [J].

Clot-Almenara, Lidia ;

Rodriguez-Escrich, Carles ;

Osorio-Planes, Laura ;

Pericas, Miguel A. .

ACS CATALYSIS, 2016, 6 (11) :7647-7651

[10] Catalytic Nucleophilic Allylation Driven by the Water-Gas Shift Reaction [J].

Denmark, Scott E. ;

Matesich, Zachery D. ;

Nguyen, Son T. ;

Sephton, Selena Milicevic .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (01) :23-48

← 1 2 3 4 5 6 7 →