Timothy F. Jamison
|Alma mater|| University of California, Berkeley |
|Institutions|| Massachusetts Institute of Technology |
|Doctoral advisor||Stuart L. Schreiber|
Timothy F. Jamison is a professor of Chemistry at the Massachusetts Institute of Technology.
Tim Jamison was born in San Jose, CA and grew up in neighboring Los Gatos, CA. He received his undergraduate education at the University of California, Berkeley. A six-month research assistantship at ICI Americas in Richmond, CA under the mentorship of Dr. William G. Haag was his first experience in chemistry research. Upon returning to Berkeley, he joined the laboratory of Prof. Henry Rapoport and conducted undergraduate research in his group for nearly three years, the majority of which was under the tutelage of William D. Lubell (now at the University of Montreal). A Fulbright Scholarship supported ten months of research in Prof. Steven A. Benner’s laboratories at the ETH in Zürich, Switzerland, and thereafter he undertook his PhD studies at Harvard University with Prof. Stuart L. Schreiber. He then moved to the laboratory of Prof. Eric N. Jacobsen at Harvard University, where he was a Damon Runyon-Walter Winchell postdoctoral fellow.
In July 1999, Jamison began his independent career at MIT, where his research program focuses on the development of new methods of organic synthesis and their implementation in the total synthesis of natural products. He was tenured in 2006.
On July 1, 2015, he became Head of MIT's Chemistry Department, saying "I am honored and delighted to have the opportunity to serve chemistry, the School of Science, and MIT.
Jamison is an organic chemist whose research is focused on the discovery and application of new reactions and technologies for organic synthesis. any of the transformations we target are based on common structural motifs or functional group patterns present in molecules provided to us by nature.
Developing effective and reliable continuous flow protocols to improve reaction yield, selectivity and minimize safety risks relative to batch conditions. Included are continuous flow protocols to prepare b-amino alcohols, tetrazoles, asymmetric ketones, cyclic carbonates and amide bonds as well as DIBAL-H reductions of esters to aldehydes, oxidation of alcohols and aldehydes, hydrogen-free alkene reductions, couplings (Ullmann condensations, Sonogashira couplings) and a variety of transformations mediated by photoredox catalysis.
Streamlining multi-step processes: telescoping two or three step reactions into a single, continuous and uninterrupted reactor network to circumvent the need for isolation and/or purification of intermediates. Some examples include developing (a) a continuous protocol for the two-carbon homologation of esters to prepare (a) β-unsaturated esters with high yield and selectivity; (b) 2-functionalized phenols via benzyne-mediated in-line generation of arylmagnesium intermediates and aerobic oxidation; (c) developing a three-step continuous flow system which integrates in-line isocyanide formation and photochemical cyclization for preparing quinoxaline derivatives and (d) a two-step glycosylation and deprotection sequence to prepare 5’-deoxyribonucleoside pharmaceuticals.
Designing integrated continuous manufacturing strategies for preparing active pharmaceutical ingredients. Within a broader context, I also been involved in developing end-to-end manufacturing processes which handle a variety of intermediate reactions, separations, crystallizations as well as drying and formulation to generate active pharmaceutical ingredients in one controlled process.
Nickel–Catalyzed Carbon–Carbon Bond Formation. The majority of the transformations under investigation are carbon–carbon bond–forming reactions promoted by nickel catalysts. We have discovered a variety of coupling reactions to join a number of different functional groups in highly regio–, stereo– and enantioselective fashion depending on the nature of the supporting ligands on nickel.
Epoxide–Opening Cascades. Over two decades ago, Koji Nakanishi proposed a provocative explanation for the structural and stereochemical similarities found across the ladder polyether family of natural products – the transformation of a polyepoxide into a ladder polyether via a cascade of epoxide–opening events. An ongoing effort in our group is the replication or emulation of such cascades. One aim is the efficient synthesis of these extremely complex natural products. In addition, we hope that our explorations into a diverse set of epoxide–opening cyclizations and cascades will shed further light on the fundamental feasibility of the Nakanishi’s hypothesis.
Target–Oriented Synthesis. In order to test the scope and the utility of newly developed methods, we strive to employ them in the total synthesis of natural products. Often these products are the original inspiration for the development of these methods. For example, we have found that nickel–catalyzed reactions are compatible with a wide array of functional groups, making them useful in complex settings, such as fragment coupling or macrocyclization operations at a late stage in synthesis.
Tim currently serves as the Associate Editor of Chemical Reviews. In 2014, he received the Council of Chemical Research Collaboration Award. Tim was awarded the MIT School of Science's Teaching Prize for Undergraduate Education in 2013, and in 2012, was named a Fellow of the Royal Society of Chemistry, receiving the Society's Merck Award that same year.
Ethers are a class of organic compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula R–O–R′, where R and R′ represent the alkyl or aryl groups. Ethers can again be classified into two varieties: if the alkyl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. A typical example of the first group is the solvent and anaesthetic diethyl ether, commonly referred to simply as "ether" (CH3–CH2–O–CH2–CH3). Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin.
Organic reactions are chemical reactions involving organic compounds. The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions, photochemical reactions and redox reactions. In organic synthesis, organic reactions are used in the construction of new organic molecules. The production of many man-made chemicals such as drugs, plastics, food additives, fabrics depend on organic reactions.
Elias James "E.J." Corey is an American organic chemist. In 1990, he won the Nobel Prize in Chemistry "for his development of the theory and methodology of organic synthesis", specifically retrosynthetic analysis. Regarded by many as one of the greatest living chemists, he has developed numerous synthetic reagents, methodologies and total syntheses and has advanced the science of organic synthesis considerably.
The Suzuki reaction is an organic reaction, classified as a cross-coupling reaction, where the coupling partners are a boronic acid and an organohalide and the catalyst is a palladium(0) complex. It was first published in 1979 by Akira Suzuki, and he shared the 2010 Nobel Prize in Chemistry with Richard F. Heck and Ei-ichi Negishi for their contribution to the discovery and development of palladium-catalyzed cross-couplings in organic synthesis. This reaction is also known as the Suzuki–Miyaura reaction or simply as the Suzuki coupling. It is widely used to synthesize polyolefins, styrenes, and substituted biphenyls. Several reviews have been published describing advancements and the development of the Suzuki reaction. The general scheme for the Suzuki reaction is shown below, where a carbon-carbon single bond is formed by coupling an organoboron species (R1-BY2) with a halide (R2-X) using a palladium catalyst and a base.
Enolates are organic anions derived from the deprotonation of carbonyl compounds. Rarely isolated, they are widely used as reagents in the synthesis of organic compounds.
A coupling reaction in organic chemistry is a general term for a variety of reactions where two fragments are joined together with the aid of a metal catalyst. In one important reaction type, a main group organometallic compound of the type R-M reacts with an organic halide of the type R'-X with formation of a new carbon-carbon bond in the product R-R'. The most common type of coupling reaction is the cross coupling reaction.
The Johnson–Corey–Chaykovsky reaction is a chemical reaction used in organic chemistry for the synthesis of epoxides, aziridines, and cyclopropanes. It was discovered in 1961 by A. William Johnson and developed significantly by E. J. Corey and Michael Chaykovsky. The reaction involves addition of a sulfur ylide to a ketone, aldehyde, imine, or enone to produce the corresponding 3-membered ring. The reaction is diastereoselective favoring trans substitution in the product regardless of the initial stereochemistry. The synthesis of epoxides via this method serves as an important retrosynthetic alternative to the traditional epoxidation reactions of olefins.
The Danishefsky Taxol total synthesis in organic chemistry is an important third Taxol synthesis published by the group of Samuel Danishefsky in 1996 two years after the first two efforts described in the Holton Taxol total synthesis and the Nicolaou Taxol total synthesis. Combined they provide a good insight in the application of organic chemistry in total synthesis.
A carbonate ester (organic carbonate or organocarbonate) is an ester of carbonic acid. This functional group consists of a carbonyl group flanked by two alkoxy groups. The general structure of these carbonates is R1O(C=O)OR2 and they are related to esters R1O(C=O)R, ethers R1OR2 and also to the inorganic carbonates.
The Darzens reaction is the chemical reaction of a ketone or aldehyde with an α-haloester in the presence of a base to form an α,β-epoxy ester, also called a "glycidic ester". This reaction was discovered by the organic chemist Auguste Georges Darzens in 1904.
The Negishi coupling is a widely employed transition metal catalyzed cross-coupling reaction. The reaction couples organic halides or triflates with organozinc compounds, forming carbon-carbon bonds (c-c) in the process. A palladium (0) species is generally utilized as the metal catalyst, though nickel is sometimes used. A variety of nickel catalysts in either Ni0 or NiII oxidation state can be employed in Negishi cross couplings such as Ni(PPh3)4, Ni(acac)2, Ni(COD)2 etc.
Organozinc compounds in organic chemistry contain carbon to zinc chemical bonds. Organozinc chemistry is the science of organozinc compounds describing their physical properties, synthesis and reactions.
The Liebeskind–Srogl coupling reaction is an organic reaction forming a new carbon–carbon bond from a thioester and a boronic acid using a metal catalyst. It is a cross-coupling reaction. This reaction was invented by and named after Jiri Srogl from the Academy of Sciences, Czech Republic, and Lanny S. Liebeskind from Emory University, Atlanta, Georgia, USA. There are three generations of this reaction, with the first generation shown below. The original transformation used catalytic Pd(0), TFP = tris(2-furyl)phosphine as an additional ligand and stoichiometric CuTC = copper(I) thiophene-2-carboxylate as a co-metal catalyst. The overall reaction scheme is shown below.
A cross-coupling reaction in organic chemistry is a reaction where two fragments are joined together with the aid of a metal catalyst. In one important reaction type, a main group organometallic compound of the type R-M reacts with an organic halide of the type R'-X with formation of a new carbon–carbon bond in the product R-R'. Cross-coupling reaction are a subset of coupling reactions. It is often used in arylations.
Strychnine total synthesis in chemistry describes the total synthesis of the complex biomolecule strychnine. The first reported method by the group of Robert Burns Woodward in 1954 is considered a classic in this research field.
The Buchner–Curtius–Schlotterbeck reaction is the reaction of aldehydes or ketones with aliphatic diazoalkanes to form homologated ketones. It was first described by Eduard Buchner and Theodor Curtius in 1885 and later by Fritz Schlotterbeck in 1907. Two German chemists also preceded Schlotterbeck in discovery of the reaction, Hans von Pechmann in 1895 and Viktor Meyer in 1905. The reaction has since been extended to the synthesis of β-keto esters from the condensation between aldehydes and diazo esters. The general reaction scheme is as follows:
William Clark Still is an American organic chemist. As a distinguished professor at Columbia University, Clark Still made significant contributions to the field of organic chemistry, particularly in the areas of natural product synthesis, reaction development, conformational analysis, macrocyclic stereocontrol, and computational chemistry. Still and coworkers also developed the purification technique known as flash column chromatography which is widely used for the purification of organic compounds.
Trifluoroperacetic acid is an organofluorine compound, the peroxy acid analog of trifluoroacetic acid, with the condensed structural formula CF
3COOOH. It is a strong oxidizing agent for organic oxidation reactions, such as in Baeyer–Villiger oxidations of ketones. It is the most reactive of the organic peroxy acids, allowing it to successfully oxidise relatively unreactive alkenes to epoxides where other peroxy acids are ineffective. It can also oxidise the chalcogens in some functional groups, such as by transforming selenoethers to selones. It is a potentially explosive material and is not commercially available, but it can be quickly prepared as needed. Its use as a laboratory reagent was pioneered and developed by William D. Emmons.
Abigail Gutmann Doyle is a Professor of Chemistry at the University of California, Los Angeles, where she holds the Saul Winstein Chair in Organic Chemistry. From 2017 to July 2021, she was the A. Barton Hepburn Professor of Chemistry at Princeton University, where she had served on the faculty since 2008. Her research focuses on the development of new chemical transformations in organic chemistry.
Paul Knochel is a French chemist and a member of the French Academy of Sciences.