Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH FRONT

Chirality Control in Photochemical Reactions: Enantioselective Formation of Complex Photoproducts in Solution

Christiane Müller A and Thorsten Bach A B
+ Author Affiliations
- Author Affiliations

A Lehrstuhl für Organische Chemie I, Department of Chemistry, Technische Universität München, 85747 Garching, Germany.

B Corresponding author. Email: thorsten.bach@ch.tum.de




Christiane Müller studied chemistry at the Technische Universität München, where she obtained her Diploma in 2007. She is currently working towards her Ph.D. in the group of T. Bach.



Thorsten Bach studied chemistry at the Universität Heidelberg and at the University of Southern California (G. A. Olah). He obtained his Ph.D. in 1991 from the Universität Marburg (M. T. Reetz). After a postdoctoral stay at Harvard University (D. A. Evans), his independent research career led him via the Universität Münster (1992–1996) and the Universität Marburg (1997–2000) to the Technische Universität München, where he has been ever since. He is an elected member of the German Academy of Science (Leopoldina) and serves as one of the regional editors of Synthesis.

Australian Journal of Chemistry 61(8) 557-564 https://doi.org/10.1071/CH08195
Submitted: 7 May 2008  Accepted: 11 June 2008   Published: 15 August 2008

Abstract

In recent years, new methods have been developed that allow for the photochemical formation of enantiomerically pure or enantiomerically enriched compounds in solution. Major strategies presented in this review rely on the use of chiral complexing agents either in a supermolecular assembly or in a defined 1:1 substrate-template complex. In addition, organocatalytic approaches and a chirality transfer from inherently chiral substrates obtained by spontaneous crystallization are discussed. Synthetic applications show that the area of enantioselective photochemistry has left the state of infancy and is about to become a mature but continuously challenging area of modern chemistry.


Acknowledgements

Our own work in this area was generously supported by the Deutsche Forschungsgemeinschaft, by Astra Zeneca (Research Award 2001 to T.B.), by Novartis (Young Investigator Award 2003 to T.B.), by Degussa (Degussa Prize for Chirality 2006 to T.B.), by the Alexander von Humboldt foundation, by the Elitenetzwerk Bayern and by the Fonds der Chemischen Industrie. T.B. wishes to thank the co-workers, who have contributed to the project and who have shown unbelievable enthusiasm in pushing this research forward. In chronological order the list of contributors includes H. Bergmann, T. Aechtner, S. Sitterberg, F. Westkämper, B. Grosch, F. Wendling, A. Bauer, S. Brandes, M. Dressel, P. Selig, S. Breitenlechner, A. Bakowski, and C. Müller.


References


[1]   Lord Kelvin W. T., Baltimore Lectures 1884 1904, pp. 436, 619 (C. J. Clay & Sons: London).

[2]   Inoue Y., Ramamurthy V. (Eds), Molecular and Supramolecular Photochemistry (Volume 11): Chiral Photochemistry 2004 (Dekker: New York, NY).

[3]   For a recent review, see: Svoboda J., König B., Chem. Rev. 2006, 106, 5413. doi:10.1021/CR050568W

[4]   (a) Photochemical reactions in the solid state are not covered in this review. For references, to zeolite photochemistry, see: V. Ramamurthy, J. Sivaguru, J. Shailaja, A. Natarajan, L. S. Kaanumalle, S. Karthikeyan, A. Joy, Molecular and Supramolecular Photochemistry (Volume 11): Chiral Photochemistry 2004, p. 563 (Eds Y. Inoue, V. Ramamurthy) (Dekker: New York, NY).
       (b) A. Corma, H. Garcia, Eur. J. Inorg. Chem. 2004,  1143.
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        |  CAS |  
         
        | Crossref |  GoogleScholarGoogle Scholar |  
         
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        |  CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        |  CAS |  
        |  CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        |  CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        |  CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  
        |  CAS |  
        | Crossref |  GoogleScholarGoogle Scholar | CAS |  open url image1