Thieme WebCheminar #25
Rising Stars in Organic Synthesis,
Session 3
2022年，Science of Synthesis成立了首届早期职业咨询委员会（Early Career Advisory Board），以了解有机化学领域一些卓越的冉冉新星的想法和观点。Thieme Chemistry Journal Awards旨在表彰那些最有前途的年轻有机化学家。
我们非常荣幸地邀请到ECAB成员和Thieme Chemistry Journal Awards获奖者作为本次化学研讨会的演讲嘉宾，分享他们最新的研究进展。本次研讨会由Gary A. Molander教授主持。
时间及注册方式
2024年4月25日 周四
00:00 北京时间
***请注意：本次研讨会将于4月24日24点，即4月25日零点开始！***
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https://cassyni.com/events/8cZhvJZ46PQ4s8nQLsXfE5/abstract
# Chair
Prof. Gary A. Molander Ph.D.
Jean d'Alembert Fellow, Laboratoire de Chimie Bioorganique, University of Paris-Saclay
# Speaker 1
Constructive Ozonolysis: Capturing Primary Ozonides
Prof. Andy Thomas
Assistant Professor, Chemistry, Texas A&M University
Abstract
Thieme Cheminars
We have found that primary ozonides have predictable lifetimes and can be harnessed as synthetic intermediates providing us an avenue to explore new carbon oxygen bond forming reactions. In this work, we describe the proof-of-principle development of a new, simple, and green syn dihydroxylation reaction through trapping primary ozonides with nucleophiles. Although there are currently many options to choose from when preparing syn-glycols a green and sustainable alternative to the transition metal-based approach is of great benefit on many fronts and its wide utility in chemistry made it the ideal reaction to launch our research program in constructive ozonolysis. Specifically, we show that primary ozonides are reactive intermediates that have definitive lifetimes at -80 C and can be captured in continuous flow. This becomes especially important because this method has virtually zero peroxide accumulation and eliminates the need to store hazardous oxidizing agents. We have demonstrated that our flow method can produce pharmaceutically relevant compounds by preparing guaifenesin, the active component in Mucinex, and a precursor to Ponesimod, a recently approved drug for multiple
# Speaker 2
Cyclopropane Synthesis using Palladium Carbenes
Prof. Sidney Wilkerson-Hill
Assistant Professor, Chemistry, University of North Carolina at Chapel Hill
Abstract
Thieme Cheminars
Methods to synthesize strained rings are a critical component of drug discovery programs. Herein, we describe a platform to obtain orphaned cyclopropanes and cyclobutanes rings using α,α-disubstituted vinyl-, crotyl- and allylhydrazone reagents. We found that the oxidation state of palladium carbene intermediate impacts the mode of carbene reactivity (i.e. cyclopropanation vs C–H insertion). Lastly, highly strained [2.1.0]-bicycles can be obtained by an intramolecular cyclopropanation reaction using Pd(0)-NHC complexes.
# Speaker 3
Access to Previously "Inaccessible" Arynes Using Transition Metals
Prof. Courtney Roberts
Assistant Professor, Department of Chemistry, University of Minnesota
Abstract
Thieme Cheminars
Research in the Roberts group involves looking at unsolved problems in organic synthesis through the perspective of organometallic/inorganic chemistry. One main area of interest for the group is the synthesis of heterocycles through aryne intermediates. Despite their useful reactivity, a number of challenges still remain in the use of arynes including problems with regioselectivity and the synthesis of N-heterocyclic arynes. Using fundamental principles of Ni chemistry, our group is the first to be able to access previously “inaccessible” 5-membered heterocyclic arynes for the first time since they were hypothesized to exist 120 years ago.
# Speaker 4
The use of C-H bond oxidations in the synthesis of natural products
Prof. Emilio de Lucca Jr.
Assistant Professor, Universidade Estadual de Campinas
Abstract
Thieme Cheminars
Selective oxidations play an important role in chemical access to more diverse products in a regio-, chemo- and diastereoselective manner. More specifically, the oxidation of C–H bonds has emerged as a powerful tool in the insertion of oxygenated functionalities at a late stage in the synthesis of complex molecules, eliminating the need for additional manipulations of functional groups. In this sense, we will show our recent efforts in the synthesis of natural diterpenes through selective oxidation reactions.
# Speaker 5
Sulfonylcyclopropanols as Modular Cyclopropanone Equivalents
Prof. Vince Lindsay
Associate Professor, Department of Chemistry, North Carolina State University
Abstract
Thieme Cheminars
Cyclopropanone derivatives have long been regarded as unusable and elusive synthetic intermediates, mainly owing to their prominent ring strain and kinetic instability. In this work, we report the stereospecific synthesis of sulfonylcyclopropanols, shown to be modular and versatile synthetic equivalents of the corresponding cyclopropanone derivatives. These reagents were found to smoothly react in a variety of reaction manifolds, including organometallic 1,2-addition affording cyclopropanols, nitrene chemistry to access chiral β-lactams, nickel-catalyzed C–C activation to cyclopentenones, as well as olefination chemistry as a general platform to chiral alkylidenecyclopropanes and other substituted cyclopropanes. Moreover, we have shown that sulfonylcyclopropanols can behave as sources of ‘C(1)-oxidized cyclopropanols’ when treated successively with amines and oxidants, effectively acting as ring-opened 3-carbon linchpin reagents. This work constitutes the first general route to enantioenriched cyclopropanone equivalents, thus unlocking a number of novel synthetic disconnections relevant to various chemical industries.
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