Design and reactivity of organic functional groups—utility of imidazolylsulfonates in the synthesis of monobactams and 3-amino nocardicinic acid

1985 ◽  
Vol 63 (12) ◽  
pp. 3613-3617 ◽  
Author(s):  
Stephen Hanessian ◽  
Claude Couture ◽  
Heinz Wyss
Keyword(s):  
Functional Groups ◽  
Intramolecular Cyclization ◽  
Leaving Group ◽  
Organic Functional Groups ◽  
Derivatives Of

The imidazolylsulfonate group has been found to be a versatile leaving group in the intramolecular cyclization of p-methoxyphenyl amides and related derivatives of N-substituted L-serine to give the corresponding β-lactams.

The Swiss army knife of biological catalysis: A compact toolkit of organic functional groups

Complexity ◽  
2006 ◽  
Vol 11 (3) ◽  
pp. 9-10 ◽  
Author(s):  
Harold J. Morowitz ◽  
Vijayasarathy Srinivasan ◽  
Eric Smith
Keyword(s):  
Functional Groups ◽  
Organic Functional Groups ◽  
Biological Catalysis

Colorimetric methods for determining organic functional groups. II

1969 ◽  
Vol 57 (4) ◽  
pp. 821-825 ◽  
Author(s):  
Walter L. Nazimowitz ◽  
T. S. Ma
Keyword(s):  
Functional Groups ◽  
Organic Functional Groups ◽  
Colorimetric Methods

ChemInform Abstract: New Derivatives of Dithiocarbamic Acid. Part 3. 3-N- Organylthiocarbamoylthio-1-propynes and Their Intramolecular Cyclization Products.

ChemInform ◽  
2010 ◽  
Vol 24 (34) ◽  
pp. no-no
Author(s):  
S. V. AMOSOVA ◽  
N. I. IVANOVA ◽  
G. A. KALABIN ◽  
S. V. ZINCHENKO ◽  
M. V. SIGALOV
Keyword(s):  
Intramolecular Cyclization ◽  
Dithiocarbamic Acid ◽  
Derivatives Of

scholarly journals Palladium-Catalyzed [3+2] Cycloaddition via Two-Fold 1,3-C(sp3)−H Activation

2020 ◽  
Author(s):  
Hojoon Park ◽  
jin-quan yu
Keyword(s):  
Functional Groups ◽  
Sulfonic Acid ◽  
Cycloaddition Reaction ◽  
Wide Range ◽  
Leaving Group ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
Overall Efficiency ◽  
Weak Coordination ◽  
Single Reaction

<div>Cycloaddition reactions provide an expeditious route to construct ring systems in a highly convergent and stereoselective manner. For a typical cycloaddition reaction to occur, however, the installation of multiple reactive functional groups (π-bonds, leaving group, etc.) are required within the substrates, compromising the overall efficiency or scope of the cycloaddition reaction. Here, we report a palladium-catalyzed [3+2] reaction that utilizes C(sp<sup>3</sup>)–H activation to generate the three-carbon unit for formal cycloaddition with maleimides. We implemented a strategy where the initial C(sp<sup>3</sup>)–H activation/olefin insertion would trigger a relayed, second remote C(sp<sup>3</sup>)–H activation to complete a formal [3+2] cycloaddition. The diastereoselectivity profile of this reaction resembles that of a typical pericyclic cycloaddition reaction in that the relationships between multiple stereocenters are exquisitely controlled in a single reaction. The key to success was the use of weakly coordinating amides as the directing group, as undesired Heck or alkylation pathways were preferred with other types of directing groups. The use of the pyridine-3-sulfonic acid ligands is critical to enable C(sp<sup>3</sup>)–H activation directed by this weak coordination. The method is compatible with a wide range of amide substrates, including lactams, which lead to novel spiro-bicyclic products. The [3+2] product is also shown to undergo a reductive desymmetrization process to access chiral cyclopentane bearing multiple stereocenters with excellent enantioselectivity.</div>

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