Synthesis and Utility of Dihydropyridine Boronic Esters

被引：51

作者：

Panda, Santanu ^{[1
]}

Coffin, Aaron ^{[1
]}

Nhu Nguyen, Q. ^{[2
]}

Tantillo, Dean J. ^{[2
]}

Ready, Joseph M. ^{[1
]}

机构：

[1] Univ Texas SW Med Ctr Dallas, Dept Biochem, Div Chem, Dallas, TX 75390 USA

[2] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 06期

关键词：

allylic compounds; boron; heterocycles; samarium iodide; synthetic methods; CROSS-COUPLING REACTIONS; C-H ARYLATION; NITROGEN-HETEROCYCLES; SAMARIUM(II) IODIDE; ORGANIC-CHEMISTRY; DIRECT ALKYLATION; NATURAL-PRODUCT; ACIDS; SECONDARY; PYRIDINES;

D O I：

10.1002/anie.201510027

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

When activated by an acylating agent, pyridine boronic esters react with organometallic reagents to form a dihydropyridine boronic ester. This intermediate allows access to a number of valuable substituted pyridine, dihydropyridine, and piperidine products.

引用

页码：2205 / 2209

页数：5

共 64 条

[11] FACILE PHOTOCHEMICAL OR OXYGEN INITIATED FREE-RADICAL CHAIN REACTIONS OF TRIALKYLBORANES WITH ORGANIC DISULFIDES - CONVENIENT NEW SYNTHESIS OF ORGANIC SULFIDES VIA HYDROBORATION [J].

BROWN, HC ;

MIDLAND, MM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (13) :3291-&

[12]

BROWN HC, 1961, J AM CHEM SOC, V83, P486, DOI 10.1021/ja01463a055

[13] Synthesis of Pyridine and Dihydropyridine Derivatives by Regio- and Stereoselective Addition to N-Activated Pyridines [J].

Bull, James A. ;

Mousseau, James J. ;

Pelletier, Guillaume ;

Charette, Andre B. .

CHEMICAL REVIEWS, 2012, 112 (05) :2642-2713

[14] Assembly-line synthesis of organic molecules with tailored shapes [J].

Burns, Matthew ;

Essafi, Stephanie ;

Bame, Jessica R. ;

Bull, Stephanie P. ;

Webster, Matthew P. ;

Balieu, Sebastien ;

Dale, James W. ;

Butts, Craig P. ;

Harvey, Jeremy N. ;

Aggarwal, Varinder K. .

NATURE, 2014, 513 (7517) :183-188

[15] A solution to the 2-pyridyl organometallic cross-coupling problem:: Regioselective catalytic direct arylation of pyridine N-oxides [J].

Campeau, LC ;

Rousseaux, S ;

Fagnou, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) :18020-18021

[16]

Chen Q., 2014, ANGEW CHEM, V126, P8891

[17] Transition-Metal-Free BF3-Mediated Oxidative and Non-Oxidative Cross-Coupling of Pyridines [J].

Chen, Quan ;

Leon, Thierry ;

Knochel, Paul .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (33) :8746-8750

[18] Transition-Metal-Free BF3-Mediated Regioselective Direct Alkylation and Arylation of Functionalized Pyridines Using Grignard or Organozinc Reagents [J].

Chen, Quan ;

du Jourdin, Xavier Mollat ;

Knochel, Paul .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (13) :4958-4961

[19] REGIOSELECTIVE SUBSTITUTION IN AROMATIC 6-MEMBERED NITROGEN-HETEROCYCLES [J].

COMINS, DL ;

OCONNOR, S .

ADVANCES IN HETEROCYCLIC CHEMISTRY, 1988, 44 :199-267

[20] THE SAMARIUM GRIGNARD REACTION - INSITU FORMATION AND REACTIONS OF PRIMARY AND SECONDARY ALKYLSAMARIUM(III) REAGENTS [J].

CURRAN, DP ;

TOTLEBEN, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (15) :6050-6058

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