Carbohydrate-Catalyzed Enantioselective Alkene Diboration: Enhanced Reactivity of 1,2-Bonded Diboron Complexes

被引：92

作者：

Fang, Lichao ^{[1
]}

Yan, Lu ^{[1
]}

Haeffner, Fredrik ^{[1
]}

Morken, James P. ^{[1
]}

机构：

[1] Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 08期

关键词：

N-HETEROCYCLIC CARBENES; ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITIONS; CHIRAL DIOLS; ESTERS; KETONES; ENONES; ALDEHYDES;

D O I：

10.1021/jacs.5b13174

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Catalytic enantioselective diboration of alkenes is accomplished with readily available carbohydrate-derived catalysts. Mechanistic experiments suggest the intermediacy of 1,2-bonded diboronates.

引用

页码：2508 / 2511

页数：4

共 28 条

[1] Structural characterization of borate esters in which sodium acts as a support to the structural framework [J].

Bishop, M ;

Bott, SG ;

Barron, AR .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2000, (18) :3100-3105

[2] Hydroxyl-Directed Stereoselective Diboration of Alkenes [J].

Blaisdell, Thomas P. ;

Caya, Thomas C. ;

Zhang, Liang ;

Sanz-Marco, Amparo ;

Morken, James P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (26) :9264-9267

[3] Asymmetric organocatalytic diboration of alkenes [J].

Bonet, Amadeu ;

Sole, Cristina ;

Gulyas, Henrik ;

Fernandez, Elena .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (33) :6621-6623

[4] Transition-Metal-Free Diboration Reaction by Activation of Diboron Compounds with Simple Lewis Bases [J].

Bonet, Amadeu ;

Pubill-Ulldemolins, Cristina ;

Bo, Caries ;

Gulyas, Henrik ;

Fernandez, Elena .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (31) :7158-7161

[5] Metal-Free Catalytic Boration at the β-Position of α,β-Unsaturated Compounds: A Challenging Asymmetric Induction [J].

Bonet, Amadeu ;

Gulyas, Henrik ;

Fernandez, Elena .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (30) :5130-5134

[6] The Growing Impact of Catalysis in the Pharmaceutical Industry [J].

Busacca, Carl A. ;

Fandrick, Daniel R. ;

Song, Jinhua J. ;

Senanayake, Chris H. .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (11-12) :1825-1864

[7]

Cade I. A., 2015, J CHEM SOC DA, V44, P7506

[8] Structural studies of bis-catecholate, bis-dithiocatecholate, and tetraalkoxy diborane(4) compounds [J].

Clegg, W ;

Elsegood, MRJ ;

Lawlor, FJ ;

Norman, NC ;

Pickett, NL ;

Robins, EG ;

Scott, AJ ;

Nguyen, P ;

Taylor, NJ ;

Marder, TB .

INORGANIC CHEMISTRY, 1998, 37 (20) :5289-5293

[9] Platinum-catalysed 1,4-diboration of 1,3-dienes [J].

Clegg, W ;

Johann, TRF ;

Marder, TB ;

Norman, NC ;

Orpen, AG ;

Peakman, TM ;

Quayle, MJ ;

Rice, CR ;

Scott, AJ .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1998, (09) :1431-1438

[10] Scope and Mechanism of the Pt-Catalyzed Enantioselective Diboration of Monosubstituted Alkenes [J].

Coombs, John R. ;

Haeffner, Fredrik ;

Kliman, Laura T. ;

Morken, James P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (30) :11222-11231

← 1 2 3 →