IDENTIFYING DATA

2013_14

Subject (*)

ASYMMETRIC SYNTHESIS

Code

13685204

Study programme

Synthesis, Catalysis and Molecular Design (2013)

Cycle

2nd

Descriptors

Credits

Type

Year

Period

4.5

Optional

Only annual

Language

Anglès

Department

Analytical Chemistry and Organic Chemistry
Physical and Inorganic Chemistry

Coordinator

DÍAZ GIMÉNEZ, MARÍA YOLANDA

E-mail

yolanda.diaz@urv.cat
paolo.melchiorre@urv.cat

Lecturers

DÍAZ GIMÉNEZ, MARÍA YOLANDA

MELCHIORRE ,-, PAOLO

Web

General description and relevant information

Adquirir coneixements avançats de l'estereoquímica dels compostos orgànics i organometàl.lics, així com diferents procediments utilitzats en síntesi asimètrica.

Competences

Type A	Code	Competences Specific
		Common
	AC1	Make correct use of modern techniques for characterizing chemical compounds.
	AC2	Develop a thorough knowledge of the most advanced applications in synthesis and catalysis.
	AC3	Correctly apply the most advanced methodologies in synthesis and catalysis.
	AC6	Have a fluent command of the specialized terminology in English related to the fields of synthesis, catalysis and molecular design.
	AC8	Design synthesis routes for new products using modern techniques of chemical synthesis, chemical and physical structural characterization, high performance experimentation, data analysis and computational chemistry.
	AC9	Develop a thorough knowledge of the modern techniques for discovering and optimizing new synthetic processes and new catalysers.
Type B	Code	Competences Transversal
		Common
	BC1	Use initiative to autonomously integrate different theories and models into a personal and creative synthesis adapted to personal professional needs.
	BC2	Solve complex problems in multidisciplinary contexts related to the field of study.
	BC3	Apply critical, logical, creative and cutting-edge thinking in a research context.
	BC4	Carry out in-depth bibliographical searches, and write reports and research proposals.
	BC6	Communicate information, ideas, problems and solutions in a clear and effective manner in spoken and written English.
Type C	Code	Competences Nuclear
		Common
	CC1	Make sophisticated use of advanced information and communication technologies.
	CC2	Manage information and knowledge.
	CC3	Act in an ethical and socially responsible manner both as a citizen and as a professional.

Learning aims

Objectives	Competences
	AC1 AC2 AC3 AC6 AC8 AC9	BC1 BC2 BC3 BC4 BC6	CC1 CC2 CC3
Understanding the advanced aspects of the stereochemistry of organic and organometallic compounds, tropism, prochirality, etc.
Understanding the methods of assymetric synthesis based on transition metals, organic catalysis, enzymatic catalysis, and the industrial procedures currently used in catalysis.
Applying the current techniques for determining enantiomeric excess, and understanding their advantages and limitations.
Designing synthetic schemes that incorporate asymmetric synthesis processes.

Contents

Topic	Sub-topic
1. Stereochemistry of organic compounds. Prochirality and prostereoisomerism. Homotopy and heterotopy. Nomenclature of stereoheterotopic groups and faces The concept of conformation. Conformational analysis Working methods in conformational analysis. Absolute configuration and relative configuration. Determining absolute configuration.
2. Introduction to asymmetric synthesis - Strategies in the synthesis of enantiomerically enriched compounds. Racemate resolution and asymmetric synthesis. Methods for determining enantiomeric excess. Specific optic rotation, gas and liquid chromotography, nuclear magnetic ressonance.
3. Use of chiral auxiliaries - Chiral Auxiliaries. Introduction. -Asymmetric additions to carbonyls. Analysis of possibilities. Alkylation of enolates - a representative example. Chiral auxiliaries in acids and derivatives. Chiral auxiliaries in aldehydes and ketones. Effective methods using chiral auxiliaries.
4. Asymmetric reagents - Enantioselective protonations and deprotonations. Reducing agents of boron and aluminium. Allylation reactions with B and Ti reagents. Chiral organometallics reagents of Zn and Cu. Expoxidation with chiral dioxiranes
5. Asymmetric catalysis with metals: hydrogenation (alkenes, ketones, imines), oxidation, other reactions (allylic alkylation, allylation, hydroboration, Heck, etc.). Reactions catalysed by Lewis acids. Ketone reduction catalysed by oxazaborolidines.
6. Organocatalysis. Reactions catalysed by acids and bases.
7. Enzymatic catalysis. Dynamic enzymatic resolution.
8. Industrial methods. Examples of the use of different asymmetric synthesis strategies Integrated discussion and compared analysis.

Planning

Methodologies :: Tests

Competences

(*) Class hours

Hours outside the classroom

(**) Total hours

Introductory activities

1

0

1

Lecture

36

72

108

Problem solving, classroom exercises

12

24

36

Personal tuition

1

0

1

Objective short-answer tests

4

0

4

(*) On e-learning, hours of virtual attendance of the teacher.
(**) The information in the planning table is for guidance only and does not take into account the heterogeneity of the students.

Methodologies

	Description
Introductory activities	Presentation of the subject.
Lecture	Presentation of subject contents.
Problem solving, classroom exercises	Extension and discussion of the lecture contents
Personal tuition	Time that each teacher has to speak to pupils and resolve their doubts.

Personalized attention

Personal tuition

Description

E-mails: -Dra. Yolanda Díaz: yolanda.diaz@urv.cat

Assessment

	Description	Weight
Problem solving, classroom exercises	Throughout the course students will leave the board to discuss the issues that must be given in advance	20%
Objective short-answer tests	At the end of the course they will receive a sheet of problems that must be submitted in stipulated time	80%

Other comments and second exam session
System of continuous assessment, divided as follow: -Problem solving, classroom exercices: 20% -Written final test: 80% The second call will be the 2nd half of May

Sources of information

Basic	Ager, D.J.; East, M.B. , Asymmetric Synthetic Methodology, CRC Press, 1996 Astruc, D. ed., Méthodes et techniques de la chimie organique, Presses Uiversitaires de Grenoble, 1999 Atkinson, R., Stereoselective synthesis, John-Wiley, 1995 Bäckvall, J.-E. , Modern Oxidation Methods, Wiley-VCH, 2004 Berkessel, A.; Gröger, H., Asymmetric Organocatalysis. From Biomimetic Concepts to Applications in Asymmetric Synthesis, Wiley-VCH, 2005 Boger, D.L., Modern Organic Synthesis, TSRI Press, 1999 Brückner, R., dvanced Organic Chemistry, A Hartcourt Academic Press, 2002 Carey, F. A.; Sundberg, R. J., Advanced Organic Chemistry, part A and B, Springer, 2007 Carreira, E.; Kvaerno, L., Classics in Stereoselective Synthesis, Wiley-VCH, 2009 Carruthers, W.; Coldham, I., Modern Methods of Organic Synthesis, Cambridge University Press, 4th Ed., 2004 Christmann, M.; Bräse, S., Asymmetric Synthesis. The Essentials, 2 nd edition, Wiley-VCH, 2008 Collins, A.N.; Sheldrake, G.N.; Crosby, J., Chirality in Industry, John Wiley, 1992 Collins, A.N.; Sheldrake, G.N.; Crosby. J. , Chirality in Industry, John Wiley , 1997 Crabtree, R. H., The Organometallic Chemistry of the Transition Metals, Wiley, 2005 Dalko, P.I., Enantioselective Organocatalysis. Reactions and Experimental Procedures, Wiley-VCH, 2007 Eliel; E.L.; Wilen, S.H., Stereochemistry of organic compounds, Wiley Interscience, 1994 Jacobsen, E.N.; Pfaltz, A.; Yamamoto. H., Comprehensive Asymmetric Catalysls I-III, Springer, 1999 Katsuki, T. , Asymmetric Oxidation Reactions, Oxford University Press, 2001 Lin, Q.G.; li, Y.M.; Chan, A.S.C., Principles and applications of asymmetric synthesis', Wiley, 2001 Mahrwald, R. , Modern Aldol Reactions 2 volumes, Wiley-VCH, 2004 Mikami, K.; Lautens, M. , New Frontiers in Asymmetric Catalysis, Wiley, 2007 Ojma, I. , Catalytic Asymmetric Synthesis, John Wiley, 2nd ed., 2000 Procter, G., Asymmetric synthesis, Oxford University press, 1996 Procter, G. , Stereoselectivity in Organic Synthesis, Oxford University press , 1998 Rizzacasa.M.A., Stoichiometric asymmetric synthesis, Sheffleld Academic Press, Blackwell Sclence, 2000 Seyden-Penne, J.; Curran, D.P., Chiral auxiliaries and ligands in asymmetric synthesis, John Wiley, 1995 Stephenson, G.R. ed., Advanced Asymmetric Synthesis, Blackie Academic and Professlonal, 1996 Walsh, P.; Kowzlowski, M., Fundamentals of Asymmetric Catalysis, University Science Books, 2009 Ward, R.S., Selectivity in Organic Synthesis, John Wiley , 1999

Complementary

Recommendations

(*)The teaching guide is the document in which the URV publishes the information about all its courses. It is a public document and cannot be modified. Only in exceptional cases can it be revised by the competent agent or duly revised so that it is in line with current legislation.