Enantioselective Construction of Acyclic Quaternary Carbon Stereocenters: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Amide Enolates

被引：95

作者：

Starkov, Pavel ^{[1
,2
,4
]}

Moore, Jared T. ^{[3
]}

Duquette, Douglas C. ^{[3
]}

Stoltz, Brian M. ^{[3
]}

Marek, Ilan ^{[1
,2
]}

机构：

[1] Technion Israel Inst Technol, Schulich Fac Chem, Mallat Family Lab Organ Chem, IL-32000 Haifa, Israel

[2] Technion Israel Inst Technol, Lise Meitner Minerva Ctr Computat Quantum Chem, IL-32000 Haifa, Israel

[3] CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA

[4] Tallinn Univ Technol, Dept Chem & Biotechnol, EE-12618 Tallinn, Estonia

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2017年 / 139卷 / 28期

基金：

以色列科学基金会;

关键词：

ASYMMETRIC CONJUGATE ADDITION; PRACTICAL CHIRAL AUXILIARY; C-C BONDS; STEREOGENIC CENTERS; STEREOSELECTIVE FORMATION; TRISUBSTITUTED ENONES; ALKYLZIRCONIUM REAGENTS; ALDOL PRODUCTS; SYSTEMS; ACIDS;

D O I：

10.1021/jacs.7b04086

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report a divergent and modular protocol for the preparation of acyclic molecular frameworks containing newly created quaternary carbon stereocenters. Central to this approach is a sequence composed of a (1) regioselective and-retentive preparation of allyloxycarbonyl-trapped fully substituted stereodefined amide enolates and of a (2) enantioselective palladium-catalyzed decarboxylative allylic alkylation reaction using a novel bisphosphine ligand.

引用

页码：9615 / 9620

页数：6

共 67 条

[1] Catalytic Asymmetric Allylboration of Indoles and Dihydroisoquinolines with Allylboronic Acids: Stereodivergent Synthesis of up to Three Contiguous Stereocenters [J].