4.8 Article

Control of Transient Aluminum-Aminals for Masking and Unmasking Reactive Carbonyl Groups

Journal

ORGANIC LETTERS
Volume 15, Issue 12, Pages 3082-3085

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol401265a

Keywords

-

Funding

  1. Purdue University
  2. Midwest Crossroads Alliance for Graduate Education and the Professoriate

Ask authors/readers for more resources

A new reagent, the dimethylaluminum N, O-dimethylhydroxylamine complex, Is effective at masking reactive carbonyl groups in situ from nucleophilic addition. This reagent allows chemoselective addition of reducing reagents, Grignard reagents, organolithiums, Wittig reagents, and enolates Into substrates with multiple carbonyl groups. Moreover, the trapped carbonyl group, a stable aminal, can be unmasked In situ for additional synthetic manipulations.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.8
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

Article Oncology

In vitro characterization of transport and metabolism of the alkaloids: vincamine, vinpocetine and eburnamonine

Tamer E. Fandy, Inas Abdallah, Maan Khayat, David A. Colby, Hazem E. Hassan

CANCER CHEMOTHERAPY AND PHARMACOLOGY (2016)

Article Chemistry, Medicinal

Activation of the γ-Aminobutyric Acid Type B (GABAB) Receptor by Agonists and Positive Allosteric Modulators

Katie M. Brown, Kuldeep K. Roy, Gregory H. Hockerman, Robert J. Doerksen, David A. Colby

JOURNAL OF MEDICINAL CHEMISTRY (2015)

Article Chemistry, Medicinal

15-Methylene-Eburnamonine Kills Leukemic Stem Cells and Reduces Engraftment in a Humanized Bone Marrow Xenograft Mouse Model of Leukemia

Dilini C. Gunasekara, Mary M. Zheng, Tara Mojtahed, James R. Woods, Tamer E. Fandy, Mark V. Riofski, Carlotta A. Glackin, Hazem E. Hassan, Julia Kirshner, David A. Colby

CHEMMEDCHEM (2016)

Article Nursing

Energy Drinks: Implications for the Breastfeeding Mother

Janet Thorlton, Azza Ahmed, David A. Colby

MCN-THE AMERICAN JOURNAL OF MATERNAL-CHILD NURSING (2016)

Article Chemistry, Organic

Optimized synthesis of a pentafluoro-gem-diol and conversion to a CF2Br-glucopyranose through trifluoroacetate-release and halogenation

Robert A. Hazlitt, Jinu P. John, Que-Lynn Tran, David A. Colby

TETRAHEDRON LETTERS (2016)

Article Chemistry, Organic

Generation of Magnesium Pentafluoropropen-2-olate from Hexafluoroisopropanol and Synthesis of 2,2,4,4,4-Pentafluoro-3,3-dihydroxyketones

Robert A. Hazlitt, Que-Lynn Tran, Munia F. Sowaileh, David A. Colby

JOURNAL OF ORGANIC CHEMISTRY (2017)

Article Chemistry, Organic

Conversion of methyl ketones and methyl sulfones into α-deutero-α,α-difluoromethyl ketones and α-deutero-α,α-difluoromethyl sulfones in three synthetic steps

Munia F. Sowaileh, Changho Han, Robert A. Hazlitt, Eun Hoo Kim, Jinu P. John, David A. Colby

TETRAHEDRON LETTERS (2017)

Article Chemistry, Organic

Magnesium-Promoted Additions of Difluoroenolates to Unactivated Imines

Alex L. Nguyen, Hari R. Khatri, James R. Woods, Cassidy S. Baldwin, Frank R. Fronczek, David A. Colby

JOURNAL OF ORGANIC CHEMISTRY (2018)

Article Chemistry, Organic

Controlling the Cleavage of Carbon-Carbon Bonds To Generate α,α-Difluorobenzyl Carbanions for the Construction of Difluoromethylbenzenes

Hari R. Khatri, Changho Han, Erica Luong, Xiaoliang Pan, Amna T. Adam, Maali D. Alshammari, Yihan Shao, David A. Colby

JOURNAL OF ORGANIC CHEMISTRY (2019)

Article Chemistry, Medicinal

Synthesis, biological evaluation, and NMR studies of 3-fluorinated derivatives of 3′,4′,5′-trihydroxyflavone and 3′,4′,5′-trimethoxyflavone

Maali D. Alshammari, Pavel V. Kucheryavy, Nicole M. Ashpole, David A. Colby

Summary: The synthesis of flavones with fluorine substitutions has been reported, and their biological evaluation showed enhanced antioxidant activity and conserved neuroprotective activity compared to their non-fluorinated counterparts. Additionally, 3-fluoro-3',4',5'-trihydroxyflavone can serve as an NMR probe to detect structural changes during its action as a radical scavenger.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2021)

Article Chemistry, Organic

Synthesis of Difluorinated Halohydrins by the Chemoselective Addition of Difluoroenolates to α-Haloketones

Munia F. Sowaileh, Maali D. Alshammari, David A. Colby

Summary: This study demonstrates the use of difluoroenolates to synthesize difluorinated bromohydrins and chlorohydrins from alpha-haloketones under mild conditions without any cyclization or rearrangement.

ORGANIC LETTERS (2021)

Article Chemistry, Medicinal

Comparison of Conformational Analyses of Naturally Occurring Flavonoid-O-Glycosides with Unnatural Flavonoid-CF2-Glycosides Using Molecular Modeling

Reem A. Alkhodier, Sushil K. Mishra, Robert J. Doerksen, David A. Colby

Summary: Glycosylated natural products display biological activity but are deglycosylated by metabolic processes. CF2-derivatives of natural products are challenging to synthesize. Difluorinated molecules have unique conformational behavior due to changes in the glycosidic linkage. The site of glycosylation and substitution pattern on the flavonoid determine the conformational properties. Docking study showed potential for flavonoid-CF2-glycosides to retain a similar binding pose as the parent O-glycoside.

JOURNAL OF CHEMICAL INFORMATION AND MODELING (2023)

Article Chemistry, Multidisciplinary

Generation of formaldehyde and formaldehyde-d2 for hydroxymethylations and hydroxydeuteromethylations of difluoroenolates and difluorobenzyl carbanions

Hari R. Khatri, Changho Han, Reem A. Alkhodier, Amna T. Adam, Baharul Islam, David A. Colby

Summary: A method for in situ production of formaldehyde and its application in reactions with specific substances are reported in this study. Mechanistic and computational studies have also characterized the formation of difluorinated organic molecules.

CHEMICAL COMMUNICATIONS (2022)

Review Chemistry, Medicinal

Application of the Pentafluorosulfanyl Group as a Bioisosteric Replacement

Munia F. Sowaileh, Robert A. Hazlitt, David A. Colby

CHEMMEDCHEM (2017)

No Data Available