Synthesis and utility of dihydropyridine boronic esters

Santanu Panda; Aaron Coffin; Q. Nhu Nguyen; Dean J. Tantillo; Joseph M. Ready

doi:10.1002/anie.201510027

Synthesis and utility of dihydropyridine boronic esters

Santanu Panda, Aaron Coffin, Q. Nhu Nguyen, Dean J. Tantillo, Joseph M. Ready

Research output: Contribution to journal › Article › peer-review

22 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	2205-2209
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	6
DOIs	https://doi.org/10.1002/anie.201510027
State	Published - Feb 5 2016

Keywords

allylic compounds
boron
heterocycles
samarium iodide
synthetic methods

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201510027

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title = "Synthesis and utility of dihydropyridine boronic esters",

abstract = "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.",

keywords = "allylic compounds, boron, heterocycles, samarium iodide, synthetic methods",

author = "Santanu Panda and Aaron Coffin and Nguyen, {Q. Nhu} and Tantillo, {Dean J.} and Ready, {Joseph M.}",

note = "Funding Information: Financial support provided by the NIH (R01GM102403) and the Welch Foundation (I-1612). X-ray crystallography performed by Dr. M. F. Yousufuddin (UT Arlington) and Dr. V. Lynch (UT Austin). NSF CHE030089 supported computational resources.",

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language = "English (US)",

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T1 - Synthesis and utility of dihydropyridine boronic esters

AU - Panda, Santanu

AU - Coffin, Aaron

AU - Nguyen, Q. Nhu

AU - Tantillo, Dean J.

AU - Ready, Joseph M.

N1 - Funding Information: Financial support provided by the NIH (R01GM102403) and the Welch Foundation (I-1612). X-ray crystallography performed by Dr. M. F. Yousufuddin (UT Arlington) and Dr. V. Lynch (UT Austin). NSF CHE030089 supported computational resources.

PY - 2016/2/5

Y1 - 2016/2/5

N2 - 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.

AB - 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.

KW - allylic compounds

KW - boron

KW - heterocycles

KW - samarium iodide

KW - synthetic methods

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DO - 10.1002/anie.201510027

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