| Author: |
Stacey L. McDonald
|
| Published in: | Springer International Publishing |
| Release Year: | 2016 |
| ISBN: | 978-3-319-38878-6 |
| Pages: | 162 |
| Edition: | First Edition |
| File Size: | 7 MB |
| File Type: | |
| Language: | English |
Description of Catalyzed Electrophilic Amidation
Catalyzed Electrophilic Amidation books a number of individuals deserve my gratitude for personal and scientific support during my time at Duke and prior to this time. I would like to mention a few. First and foremost, I must thank my husband, Michael. You have been very patient through this entire process, and without your love and support, I can’t imagine how I would have survived these past 6 years. I am also grateful to my mom and dad, Carolyn and Michael Turner. Thank you for your encouragement and support in all my academic pursuits and for always pushing me to be my best, both personally and academically.
I would also like to extend my gratitude to my research advisor, Qiu Wang. Thank you for taking me in and pushing me to be the best scientist I could be each and every day. Your guidance and encouragement over the past 3 years have been greatly appreciated. It has been a distinct privilege working with you, and I am extremely grateful for this experience.
Lastly, I need to thank my fellow graduate students who have worked with me in the Wang laboratory. To Chuck Hendrick, Jerry Ortiz, and Lily Du: You guys have been there since the beginning, and it has been wonderful to work with you. I couldn’t imagine better people to have by my side going through this experience. Thank you so much for being there through the research lows and highs and for putting up with me. Thanks also to the rest of the Wang laboratory, and you have all helped me in various ways and made my time spent in the laboratory even more worthwhile. Again, thank you to all of those who have supported me through my time in graduate school.
I would also like to extend my gratitude to my research advisor, Qiu Wang. Thank you for taking me in and pushing me to be the best scientist I could be each and every day. Your guidance and encouragement over the past 3 years have been greatly appreciated. It has been a distinct privilege working with you, and I am extremely grateful for this experience.
Lastly, I need to thank my fellow graduate students who have worked with me in the Wang laboratory. To Chuck Hendrick, Jerry Ortiz, and Lily Du: You guys have been there since the beginning, and it has been wonderful to work with you. I couldn’t imagine better people to have by my side going through this experience. Thank you so much for being there through the research lows and highs and for putting up with me. Thanks also to the rest of the Wang laboratory, and you have all helped me in various ways and made my time spent in the laboratory even more worthwhile. Again, thank you to all of those who have supported me through my time in graduate school.
Content of Catalyzed Electrophilic Amidation
1 Electrophilic Amination for the Synthesis of Alkyl and Aryl
Amines .................................................. 1
1.1 Synthesis of Amines via C–N Bond Formation ............... 1
1.1.1 Electrophilic Amination Reagents and Reactions ........ 3
1.1.2 Direct Electrophilic Amination of C–H Bonds .......... 11
1.1.3 Conclusions..................................... 16
References................................................ 18
2 Selective a-Amination and a-Acylation of Esters and Amides
via Dual Reactivity of O-Acylhydroxylamines Toward Zinc
Enolates ................................................. 25
2.1 a-Functionalization of Esters and Amides ................... 25
2.1.1 a-Amination of Carbonyl Compounds ................ 25
2.1.2 a-Acylation of Carbonyl Compounds ................. 31
2.1.3 Zinc Enolates for a-Functionalization
of Carbonyl Compounds........................... 32
2.2 Results and Discussion .................................. 32
2.2.1 Electrophilic Amination and Acylation of Esters
and Amides via Zinc Enolates....................... 32
2.2.2 Initial Amination Studies Using the Reformatsky
Reagent........................................ 33
2.2.3 Amination Studies Using Zn(tmp)2 for Zinc
Enolate Formation................................ 35
2.2.4 a-Acylation of Ester and Amide Zinc Enolates.......... 38
2.2.5 Proposed Mechanism for the a-Amination
and a-Acylation Reactions ......................... 41
2.3 Conclusion ........................................... 43
2.3.1 Supplemental Information .......................... 43
2.3.2 Characterization of Compounds ..................... 46
References................................................ 56
Amines .................................................. 1
1.1 Synthesis of Amines via C–N Bond Formation ............... 1
1.1.1 Electrophilic Amination Reagents and Reactions ........ 3
1.1.2 Direct Electrophilic Amination of C–H Bonds .......... 11
1.1.3 Conclusions..................................... 16
References................................................ 18
2 Selective a-Amination and a-Acylation of Esters and Amides
via Dual Reactivity of O-Acylhydroxylamines Toward Zinc
Enolates ................................................. 25
2.1 a-Functionalization of Esters and Amides ................... 25
2.1.1 a-Amination of Carbonyl Compounds ................ 25
2.1.2 a-Acylation of Carbonyl Compounds ................. 31
2.1.3 Zinc Enolates for a-Functionalization
of Carbonyl Compounds........................... 32
2.2 Results and Discussion .................................. 32
2.2.1 Electrophilic Amination and Acylation of Esters
and Amides via Zinc Enolates....................... 32
2.2.2 Initial Amination Studies Using the Reformatsky
Reagent........................................ 33
2.2.3 Amination Studies Using Zn(tmp)2 for Zinc
Enolate Formation................................ 35
2.2.4 a-Acylation of Ester and Amide Zinc Enolates.......... 38
2.2.5 Proposed Mechanism for the a-Amination
and a-Acylation Reactions ......................... 41
2.3 Conclusion ........................................... 43
2.3.1 Supplemental Information .......................... 43
2.3.2 Characterization of Compounds ..................... 46
References................................................ 56
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