Play all audios:
ABSTRACT Thalidomide comes in two forms: a left-handed compound which is a powerful tranquilizer, and a right-handed version which can disrupt fetal development causing severe handicap. As a
necessary consequence of synthetic methods available in the early 1960s the two forms were present in equal proportions in the manufactured drug, with catastrophic consequences. The
thalidomide story is perhaps the most painful reminder of the importance of stereochemistry—the spatial ordering of groups in a molecule can be as influential as the chemical nature of the
groups themselves. A principal problem in organic synthesis is, therefore, the development of methods for producing complex molecules with a stereochemically defined structure. Access
through your institution Buy or subscribe This is a preview of subscription content, access via your institution ACCESS OPTIONS Access through your institution Subscribe to this journal
Receive 51 print issues and online access $199.00 per year only $3.90 per issue Learn more Buy this article * Purchase on SpringerLink * Instant access to full article PDF Buy now Prices may
be subject to local taxes which are calculated during checkout ADDITIONAL ACCESS OPTIONS: * Log in * Learn about institutional subscriptions * Read our FAQs * Contact customer support
SIMILAR CONTENT BEING VIEWED BY OTHERS CATALYTIC ASYMMETRIC SYNTHESIS OF _META_ BENZENE ISOSTERES Article 21 August 2024 CHEMICAL SYNTHESIS AS A DISCOVERY PLATFORM IN IMMUNOSUPPRESSION AND
DETERMINATION OF MODE OF ACTION Article 04 January 2024 MODULAR, AUTOMATED SYNTHESIS OF SPIROCYCLIC TETRAHYDRONAPHTHYRIDINES FROM PRIMARY ALKYLAMINES Article Open access 04 October 2023
REFERENCES * Pratt, A. J., Davies, S. G., Brown, J. M. & Fleet, G. W. J. _Chemy Br._ 25, 259–268 (1989). Google Scholar * Morrison, J. D. (ed.) _Asymmetric Synthesis_ Vol 1–5 (Wiley,
New York, 1983–5). * Brunner, H. _Topics Stereochem._ 18, 129–248 (1988). CAS Google Scholar * Jacques, J., Wilen, S. H. & Collet, A. _Enantiomers, Racemates and Resolutions_ (Wiley,
New York, 1981). Google Scholar * Evans, D. A., Chapman, K. T. & Bisaha, J. _J. Am. chem. Soc._ 110, 1238–1256 (1988). Article CAS Google Scholar * Gao, Y. _et al._ _J. Am. chem.
Soc._ 109, 5765–5777 (1987). Article CAS Google Scholar * Fleet, G. W. J., Ransden, N. G. & Witty, D. R. _Tetrahedron_ 45, 327–336 (1989). Article CAS Google Scholar * Davies, S.
G. _et al._ _Phil. Trans. R. Soc._ A326, 619–631 (1988). Article ADS CAS Google Scholar * Davies, S. G. _Pure appl. Chem._ 60, 13–20 (1988). Article CAS Google Scholar * Davies, S. G.
_et al._ _Bull. Soc. chim. Fr._ 608–630 (1987). * Bashiardes, G. & Davies, S. G. _Tetrahedron Lett._ 28, 5563–5564 (1987). Article CAS Google Scholar * Brown, S. L., Davies, S. G.,
Foster, D. F., Seeman, J. I. & Warner, P. _Tetrahedron Lett._ 27, 623–626 (1986). Article CAS Google Scholar * Porter, R. & Clark, S. (eds) _Enzymes in Organic Synthesis, Ciba
Foundation Symp. 111_ (Pitman, London, 1985). * Schneider, M. P. (ed.) _Enzymes as Catalysts in Organic Synthesis_ (Riedel, Dordrecht, 1986). Google Scholar * Jones, J. B. _Tetrahedron_ 42,
3351–3400 (1986). Article CAS Google Scholar * Yamada, H. & Shimizu, S. _Angew. Chem. Int. Edn Engl._ 27, 622–640 (1988). Article Google Scholar * Pratt, A. J. _Chemy Br._ 25,
282–287 (1989). CAS Google Scholar * Bednarski, M. D. _et al._ _J. Am. chem. Soc._ 111, 627–635 (1989). Article CAS Google Scholar * Kagan, H. B. _Comprehensive Organometallic
Chemistry_ Vol. 8, 560–600 (eds Wilkinson, G., Stone, F. G. A. & Abel, E. W.) (Pergamon, Oxford, 1982). Google Scholar * Brown, J. M. & Chaloner, P. _Catalysis with Metal-Phosphine
Complexes_ Ch. 4, 131–170 (ed. Pignolet, L.) (Plenum, New York, 1984). Google Scholar * James, B. R. _Comprehensive Organometallic Chemistry_ Vol. 8, Ch. 51 (eds Wilkinson, G., Stone, F. G.
A. & Abel, E. W.) (Pergamon, Oxford, 1982). Google Scholar * Takaya, H. _et al._ _J. Am. chem. Soc._ 109, 1596–1598 (1987). Article CAS Google Scholar * Kitamura, M. _et al._ _J.
Am. chem. Soc._ 110, 629–631 (1988). Article CAS Google Scholar * Kagan, H. B. & Fiaud, J.-C. _Topics Stereochem._ 18, 249–330 (1988). CAS Google Scholar * Brown, J. M., Cutting, I.
& James, A. P. _Bull. Soc. chim. Fr._ 212–219 (1988). * Brown, J. M. _Angew. Chem., Int. Edn Engl._ 26, 191–204 (1987). Google Scholar * Oguni, N. & Omi, T. _Tetrahedron Lett._ 25,
2823–2827 (1984). Article CAS Google Scholar * Kitamura, M., Suga, S., Kawai, K. & Noyori, R. _J. Am. chem. Soc._ 108, 6071–6072 (1986). Article CAS Google Scholar * Soai, K.,
Ookawa, A., Kaba, T. & Ogawa, K. _J. Am. chem. Soc._ 109, 7111–7119 (1987). Article CAS Google Scholar * Noyori, R., Suga, S., Kawai, K., Okada, S. & Kitamura, M. _Pure appl.
Chem._ 60, 1597–1612 (1988). Article CAS Google Scholar * Oguni, N., Matsuda, Y. & Kaneko, T. _J. Am. chem. Soc._ 110, 7877–7879 (1988). Article CAS Google Scholar * Kitamura, A.,
Okada, S., Suga, S. & Noyori, R. _J. Am chem. Soc._ 111, 4028–4036 (1989). Article CAS Google Scholar Download references AUTHOR INFORMATION AUTHORS AND AFFILIATIONS * Dyson Perrins
Laboratory, South Parks Road, Oxford, OX1 3QY, UK John M. Brown & Stephen G. Davies Authors * John M. Brown View author publications You can also search for this author inPubMed Google
Scholar * Stephen G. Davies View author publications You can also search for this author inPubMed Google Scholar RIGHTS AND PERMISSIONS Reprints and permissions ABOUT THIS ARTICLE CITE THIS
ARTICLE Brown, J., Davies, S. Chemical asymmetric synthesis. _Nature_ 342, 631–636 (1989). https://doi.org/10.1038/342631a0 Download citation * Issue Date: 07 December 1989 * DOI:
https://doi.org/10.1038/342631a0 SHARE THIS ARTICLE Anyone you share the following link with will be able to read this content: Get shareable link Sorry, a shareable link is not currently
available for this article. Copy to clipboard Provided by the Springer Nature SharedIt content-sharing initiative