SYNFORM People, Trends and Views in Synthetic Organic Chemistry 2013/07 Thieme SYNSTORIES Efficient and Stereoselective Nitration of Mono- and Disubstituted Olefins with AgNO 2 and TEMPO Highly Efficient Cu(I)-Catalyzed Oxidation of Alcohols to Ketones and Aldehydes with Diaziridinone N-Chlorosuccinimide, an Efficient Reagent for On-Resin Disulfide Formation in Solid-Phase Peptide Synthesis Young Career Focus: Dr. AnnMarie O’Donoghue (Durham University, UK) CONTACT Your opinion about SYNFORM is welcome, please correspond if you like: [email protected]This document was downloaded for personal use only. Unauthorized distribution is strictly prohibited.
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SYNFORMPeople, Trends and Views in Synthetic Organic Chemistry
2013/07
Thieme
SYNSTORIES
Efficient and StereoselectiveNitration of Mono- and Disubsti tut edOlefins with AgNO2 and TEMPO
Highly Efficient Cu(I)-CatalyzedOxidation of Alcohols to Ketonesand Aldehydes with Diaziridinone
N-Chlorosuccinimide, an EfficientReagent for On-Resin DisulfideFormation in Solid-Phase PeptideSynthesis
Young Career Focus: Dr. AnnMarie O’Donoghue (Durham University, UK)
CONTACT
Your opinion about SYN
FORM is
welcome, please corres
pond if you like:
marketing@thieme-chem
istry.com
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Dear readers,
This issue of SYNFORM features three
SYNSTORIES from three different con-
tinents. The first one comes from India
and describes the very handy, efficient
and stereoselective nitration of olefins
developed by Professor Maiti, which
represents a very attractive alternative to the well-known
Henry nitroaldol reaction. The second SYNSTORY comes
from the USA and reports on the use of diaziridinone as an
oxidant for transforming alcohols into ketones and aldehydes,
according to the methodology developed by Professor Shi,
which is an interesting alternative to the widely used Swern
reaction. The third SYNSTORY comes from Spain and guides
us through the new protocol developed by Professor Albe ricio
for the selective construction of disulfide bridges from
cysteine-rich peptides on resin, which is an extremely valu-
able addition to the existing methods for the synthesis of
specifically folded peptides. The issue is completed by a
Young Career Focus article coming again from Europe, and
specifically from the UK, where Dr. O’Donoghue is de -
velop ing her research which is focused on catalysis at the
interface of organic and biological chemistry.
Enjoy your reading!
Editor of SYNFORM
SYNFORM A81
IN THIS ISSUE
SYNSTORIES
Efficient and Stereoselective Nitration of Mono- and Disubstituted Olefins with AgNO2
Debabrata Maiti received his PhDfrom Johns Hopkins University (USA)in 2008 under the supervision of Pro -fessor Kenneth D. Karlin. After post-doctoral studies at the Massa chusettsInstitute of Technology (Cambridge,USA) with Professor Stephen L. Buch -wald (2008–2010), he joined the De -partment of Chemistry of IIT Bombay(India) as an Assistant Professor in2011. His research interests are fo -cus ed on the development of newand sustainable synthetic methodolo-gies.
Soham Maity was born in 1988 inWest Bengal (India). He studied che-mistry at St. Xavier’s College (Kolkata,India) and received his BSc in 2009.After completing his MSc at the Uni -versity of Calcutta (India) he joinedProfessor Maiti’s group in 2011wherehe is currently a second-year PhDstudent.
Prof. D. Maiti S. Maity
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The oxidation of alcohols to aldehydes or ketones is one of
the most commonly employed chemical transformations in
organic synthesis. While numerous oxidation methods have
been developed, only a few of them are used routinely. The
development of new and efficient oxidation processes with
safe reagents under mild conditions is still highly desirable
and valuable. Recently, Professor Yian Shi and co-workers at
Colorado State University (Fort Collins, USA) reported a
novel and efficient CuBr-catalyzed oxidation of alcohols
using di-tert-butyldiaziridinone.
SYNFORM, 2013/07
Published online: 17.06.2013, DOI: 10.1055/s-0033-1338880
Yian Shi was born in Jiangsu (P. R.of China). He obtained his B.Sc.degree from Nanjing Uni ver sity (P. R.of China) in 1983, his M.Sc. degreefrom the University of Toronto (Canada)with Professor Ian W. J. Still in 1987,and his Ph.D. degree from StanfordUni ver sity (USA) with Professor BarryM. Trost in 1992. After a postdoctoralstudy at Harvard Medical School(USA) with Professor ChristopherWalsh, he joined Colorado State Uni -
versity (USA) as an Assistant Professor in 1995 and was pro-moted to Associate Professor in 2000 and Full Professor in2003. His current research interests include the developmentof new synthetic methods, asymmetric catalysis, and the syn-thesis of natural products.
Yingguang Zhu was born in Hunan(P. R. of China). He received his B.Sc.degree from Hunan Univer sity ofScience and Technology (P. R. ofChina) in 2002 and his M.Sc. degreefrom East China Normal University(Shanghai, P. R. of China) in 2005.After two years of working at WuXiAppTec Co., Ltd. (P. R. of China) as aresearch scientist, he went on toobtain his Ph.D. degree from EastChina Normal University in 2010
under the supervision of Profes sors Wenhao Hu and LipingYang. In autumn of 2010, he joined Colorado State University(USA) as a Post doctoral Fellow with Professor Yian Shi. Hiscurrent research interests include the development of novelsynthetic methodologies and asymmetric synthesis.
Baoguo Zhao was born in Hubei (P. R. of China). He received hisPh.D. degree from Shanghai Insti tuteof Organic Chemistry, Chinese Aca -demy of Sciences (P. R. of China) in2006 under the supervi sion of Prof -essor Kuiling Ding. Then, he workedwith Professor Yian Shi as a Post -doctoral Fellow for five years atColorado State University (USA). In2011, he joined Shanghai NormalUniversity (P. R. of China) as a Full
Professor. His current research interests include the develop-ment of new synthetic methodologies and novel chiral catalystsfor asymmetric reactions.
Tobias M. Postma was born in 1987 in ‘s-Hertogenbosch (TheNetherlands). He received his MSc degree in 2011 from UtrechtUniversity (The Netherlands) under the supervision of ProfessorRob Liskamp. During his MSc he spent eight months at theUniversity of Cambridge (UK) under the supervision of Dr. DavidSpring. In 2011, he joined the group of Professor FernandoAlbericio at the Institute for Research in Biomedicine in Barce -lona (Spain) where he currently is a second-year PhD student.
Fernando Albericio is Full Professor at the University ofBarcelona (Spain), Group Leader at the Institute for Research inBiomedicine (Barcelona), and Honorary Research Professor atthe University of KwalaZulu-Natal (Durban, South Africa). Hismajor research interests cover practically all aspects of peptidesynthesis and combinatorial chemistry methodologies, as wellas synthesis of peptides and small molecules with therapeuticactivities. He has published over 650 papers, several reviewarticles, more than 45 patents, and is co-author of three books.He is editor of several scientific journals and an editorial boardmember for several others. Recently, he was honored with aDoctorate Honoris Causa by the Universidad de Buenos Aires(Argentina) and the Vincent du Vigneaud Award by the Ameri -can Peptide Society.
From left: T. Postma, Prof. F. Albericio
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SYNFORM, 2013/07
Published online: 17.06.2013, DOI: 10.1055/s-0033-1338880
to time meet young up-and-coming researchers who are per-
forming exceptionally well in the arena of organic chemistry
and related fields of research, in order to introduce them to the
readership. This SYNSTORY with a Young Career Focus pre-
sents Dr. AnnMarie O’Donoghue, Durham University, UK.
INTERVIEW
SYNFORM What is the focus of your current research
activity?
Dr. A. O’Donoghue The focus of my current research is
the study of organic and biological reaction mechanisms.
Through understanding the strategies underpinning catalysis,
we aim to inform the design of improved catalyst systems.
We use a physical organic chemistry approach towards deci-
phering reaction mechanisms based on organic synthesis,
reaction kinetics, isotopic labeling and structure–activity
studies.
SYNFORM When did you get interested in synthesis?
Dr. A. O’Donoghue From early in my undergraduate stu-
dies, I enjoyed making molecules and it became clear that
synthesis underpins all areas of organic chemistry. Physical
organic chemistry has allowed me to combine my interest in
synthetic chemistry with the application of physical methods
for the determination of reaction mechanisms.
SYNFORM What do you think about the modern role and
prospects of organic synthesis?
Dr. A. O’Donoghue In the last few decades, there have
been huge developments in synthetic organic chemistry.
There now exist successful methodologies for many chal leng -
ing organic transformations and efficient catalyst systems for
numerous synthetic processes. Given these many significant
advances, the task of identifying further new organic syn -
thetic chemistry and catalyst systems is difficult. I believe
that further developments in synthetic chemistry, particularly
in catalysis, will hinge upon a deeper fundamental under-
standing of underlying mechanisms and modes of action.
Research in physical organic chemistry must keep in step
with developments in synthetic chemistry.
SYNFORM Your research group is active at the interface
of organic and biological chemistry, with a focus on cata -
l ysis. Could you tell us more about your research and its
aims?
Young Career Focus: Dr. AnnMarie O’Donoghue (Durham University, UK)
BIOGRAPHICAL SKETCH
AnnMarie O’Donoghue was bornin Dublin (Ireland) in 1973. Shestudied for her BSc degree(Chem istry) at the UniversityCollege Dublin. She remained atthe same institution for her PhDstudies in physical organic chemi-stry under the supervision of Pro -fessor Rory More O’Ferrall. HerPhD was awarded in November1999 for her research on the for-mation and reactions of reactive
carbocation intermediates. In 1999, she was awarded aFulbright Fellowship to pursue postdoctoral studies in theresearch group of Professor John Richard at the Universityat Buffalo, the State University of New York (USA). Thereshe worked on the dynamics of the proton-transfer reac -tions of triosephosphate isomerase. She returned to Uni -versity College Dublin for a brief period in 2002 as a short-term Lecturer in Organic Chemistry. In 2003, she wasaward ed a Marie Curie Fellowship for postdoctoral studieson the directed evolution of proteins with Dr. Florian Holl -felder at the Department of Biochemistry, University ofCambridge (UK). From 2004–2005, she again returned toUniversity College Dublin as a Lecturer in Organic Chem -istry. In 2005 she moved to a Lectureship in Physical Org a -nic Chemistry at the Department of Chemistry, DurhamUniversity (UK). Apart from a career break in 2008–2009due to the birth of twins, she has since remained at DurhamUniversity as an independent researcher and was promotedto Senior Lecturer in 2012. Her research focuses on mecha-nistic studies of organic and biological transformations witha special interest in organocatalysis.
Dr. A. O’Donoghue
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Dr. A. O’Donoghue Despite the large increase in the appli-
cation of small molecule organocatalysts there have been few
detailed studies of catalytic mechanisms. We are currently
studying the mechanisms of three key classes of organoca -
Figure 1 pKa Scale for the conjugate acids of N-heterocyclic carbenes in water
Matteo Zanda
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COMING SOON COMING SOON
SYNFORM 2013/08is available from July 18, 2013
In the next issues:
SYNSTORIES
Copper(II) Triflate Catalyzed tert-Butylation of Anilines(Focus on an article presented at the 245th ACS National Meeting &
Exposition, New Orleans, USA, April 2013)
Chiral Fluorinated Sulfoximines as New Fluoroalkylating Agents(Focus on an article presented at the 245th ACS National Meeting &
Exposition, New Orleans, USA, April 2013)
Hydrocupration of Terminal Alkynes: A Key Step in New CatalyticRoutes for Alkyne Hydrofunctionalization(Focus on an article presented at the 245th ACS National Meeting &
Exposition, New Orleans, USA, April 2013)
Synthesis of 1,5-Disubstituted 3-Amino-1H-1,2,4-triazoles from1,3,4-Oxadiazolium Hexafluorophosphates(Focus on an article presented at the 245th ACS National Meeting &
Exposition, New Orleans, USA, April 2013)
SYNFORM
CONTACTMatteo Zanda,NRP Chair in Medical TechnologiesInstitute of Medical SciencesUniversity of AberdeenForesterhill, Aberdeen, AB25 2ZD, UKand C.N.R. – Istituto di Chimica del Riconoscimento Molecolare,Via Mancinelli, 7, 20131 Milano, Italy,e-mail: [email protected], fax: +39 02 23993080
FURTHER HIGHLIGHTSSYNTHESISReview on: Carbon-Sulfur Bond Formation via Metal-Catalyzed Allylations of Sulfur Nucleophiles(by W. Liu, X. Zhao)
SYNLETTAccount on: When Alkyne π-Activation Meets Pinacol-Type[1,2]-Rearrangement – About the Invention of DominoReactions for the Synthesis of Carbocycles and Heterocycles(by K.-D. Umland, S. F. Kirsch)
SYNFACTSSynfact of the Month in category „Metal-CatalyzedAsymmetric Synthesis and Stereoselective Reactions“:Cr/Salen-Catalyzed Nazarov Cyclization of Dienones
EditorMatteo Zanda, NRP Chair in Medical Technologies, Institute of MedicalSciences, University of Aberdeen, Foresterhill, Aberdeen, AB25 2ZD, UKand C.N.R. – Istituto di Chimica del Riconoscimento MolecolareVia Mancinelli, 7, 20131 Milano, ItalyEditorial Assistant: Alison M. [email protected]; fax: +39 02 23993080
Publication InformationSYNFORM will be published 12 times in 2013 by Georg Thieme Verlag KG,Rüdigerstraße 14, 70469 Stuttgart, Germany, and is an additional online ser-vice for SYNTHESIS, SYNLETT and SYNFACTS.
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