Advanced Organic Synthesis

CHEM30412 Advanced Organic Synthesis 10 Semester 2 Undergraduate Level 3 Giacomo Crisenza Unit coordinator Department of Chemistry 1 FHEQ level (Framework for Higher Education Qualifications) ' Last part of a Bachelors ' European Credit Transfer & Accumulation System Rating : 5.0 To cover key transformations in depth and to put them in context in synthesis.  To cover the strategies employed in the total synthesis of complex natural products.  Appreciate how modern synthetic organic chemistry is conducted.  To cover key transformations in depth and to put them in context in synthesis.  To cover the strategies employed in the total synthesis of complex natural products.  Appreciate how modern synthetic organic chemistry is conducted.  The unit aims:To provide an up-to-date account of modern methods in synthetic organic chemistry, with an emphasis on transition metal catalysis. On successful completion of the course students should be able to:  <ul><li>Propose plausible organometallic synthetic strategies or routes to complex organic structures.  </li><li>Propose suitable reagents for given transformations.  </li><li>Be able to suggest mechanistic or strategic rationales for given synthetic routes.  </li><li>Understand the principle mechanisms of transition metal catalysed cross coupling, C-H activation, and metathesis reactions.  </li><li>Have an appreciation of the importance and value of total synthesis – beyond the context of academic research. </li></ul> Problem-solving skills that involve applying the information learned to unseen organic transformations and syntheses.  Ability to recognise disconnections and plan synthetic routes from commercially available materials.  Time management and organisational skills (ability to work independently and to work efficiently and effectively).   Organometallics in synthesis (Prof Igor Larrosa, 8 lectures)  <ul><li>Applications of main group metal complexes to organic synthesis  </li><li>Directed C-H metallation of organic substrates using organolithiums.  </li><li>Organocuprate chemistry  </li><li>Organogold catalysis for alkene and alkyne functionalisation  </li><li>Catalytic C-H activation using transition metals  </li></ul>Transition metal catalysis (Dr Michael James, 8 lectures)  <ul><li>Palladium-catalysed cross coupling using  Stille, Suzuki, and related methods  </li><li>The Heck reaction  </li><li>Palladium-catalysed C-N and C-O bond formation  </li><li>C-H activation in synthesis  </li><li>Alkene and alkyne metathesis in synthesis  </li></ul>Total Synthesis (Dr Giacomo Crisenza, 8 lectures)  <ul><li>The importance, impact and applications of total synthesis  </li><li>Planning synthesis by recognising key disconnections based on the functional groups present  </li><li>Strategic application of named and common organic reactions in complex settings  </li><li>Rationalising the stereochemical outcome of enantio- and diastereoselective transformations  </li><li>Reagents used to interconvert common functional groups  </li><li>The power of ring forming reactions and (biomimetic) cascade processes  </li><li>Use and applications of 1,2-rearrangements, oxidation protocols, radical reactions and chiral auxiliaries.  </li></ul> 1 Written exam 100% <ul><li>Students will be expected to submit tutorial problem sheets that will be marked or discussed in three-weekly tutorial / workshops.  </li><li>Revision lectures and problem sessions will be held during and/or at the beginning of each teaching block.  </li><li>Three workshops will be held at the end of the teaching session.  </li></ul> CHEM10101 Introductory Chemistry Pre-Requisite Compulsory CHEM10412 Structure and Reactivity Pre-Requisite Compulsory CHEM20412 Structure and reactivity of organic molecules Pre-Requisite Compulsory CHEM30411 Core Chemistry 1 Pre-Requisite Compulsory CHEM20411 Organic Synthesis Pre-Requisite Compulsory Y <ul><li>J. Clayden, N. Greeves, S. Warren, P. Wothers "Organic Chemistry" Oxford University Press  </li><li>J. F. Hartwig “Organotransition Metal Chemistry: From Bonding to Catalysis” University Science Books  </li><li>R. H. Crabtree “The Organometallic Chemistry of the Transition Metals” John Wiley & Sons, Inc.  </li><li>K. C. Nicolau, E. J. Sorensen “Classics in Total Synthesis: Targets, Strategies, Methods” Wiley-VCH.  </li><li>L. Kürti, B. Czakó “Strategic Applications of Named Reactions in Organic Synthesis,: Background and Detailed Mechanisms” Academic Press. </li></ul> Lectures 27 0 73 This unit is jointly taught with CHEM40412 Advanced Organic Synthesis.