Synthesis and Utility of Dihydropyridine Boronic Esters

被引：47

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 50 条

[1] Copper catalyzed radiobromination of boronic pinacol esters: utility in PARP inhibitor synthesis
Mixdorf, Jason
Hoffman, Sabrina
Aluicio-Sarduy, Eduardo
Barnhart, Todd
Engle, Jonathan
Ellison, Paul
[J]. NUCLEAR MEDICINE AND BIOLOGY, 2022, 108 : S175 - S175
[2] BORONIC ESTERS IN STEREODIRECTED SYNTHESIS
MATTESON, DS
[J]. TETRAHEDRON, 1989, 45 (07) : 1859 - 1885
[3] Boronic Esters in Asymmetric Synthesis
Matteson, Donald S.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (20): : 10009 - 10023
[4] Homologation of boronic esters with (dialkoxymethyl)lithiums.: Asymmetric synthesis of α-alkoxy boronic esters
Carmès, L
Carreaux, F
Carboni, B
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (17): : 5403 - 5408
[5] Organic boronic acids and boronic acid esters in industrial synthesis
Zenk, R
Partzsch, S
[J]. CHIMICA OGGI-CHEMISTRY TODAY, 2003, 21 (05) : 70 - 73
[6] α-halo boronic esters in asymmetric synthesis
Matteson, DS
[J]. TETRAHEDRON, 1998, 54 (36) : 10555 - 10606
[7] ASYMMETRIC-SYNTHESIS WITH BORONIC ESTERS
MATTESON, DS
SADHU, KM
RAY, R
PETERSON, ML
MAJUMDAR, D
HURST, GD
JESTHI, PK
TSAI, DJS
ERDIK, E
[J]. PURE AND APPLIED CHEMISTRY, 1985, 57 (12) : 1741 - 1748
[8] ASYMMETRIC-SYNTHESIS WITH BORONIC ESTERS
MATTESON, DS
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (08) : 294 - 300
[9] Diastereoselective Synthesis of Cyclopropyl Boronic Esters
Pietruszka, J.
Widenmeyer, M.
[J]. Synlett, (08):
[10] Diastereoselective synthesis of cyclopropyl boronic esters
Pietruszka, J
Widenmeyer, M
[J]. SYNLETT, 1997, (08) : 977 - &

← 1 2 3 4 5 →