Practical and Highly Enantioselective Ring Opening of Cyclic Meso-Anhydrides Mediated by Cinchona Alkaloids

Author:

Bolm Carsten1,Schiffers Ingo1,Dinter Christian L.1,Gerlach Arne1

Affiliation:

1. Institut für Organische Chemie der RWTH Aachen, Prof.-Pirlet-Strasse 1, D-52056 Aachen, Germany

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry

Reference73 articles.

1. Reviews:  (a) Ohno, M.; Otsuka, M.Org. React.1989,37, 1. (b) Danieli, B.; Lesma, G.; Passarella, D.; Riva, S. InAdvances in the Use of Synthons inOrganic Chemistry; Dondoni, A., Ed.; JAI Press:  London, 1993; Vol. 1, pp 143-219. (c) Wong, C.H.; Whitesides, G. M. InEnzymes in SyntheticOrganic Chemistry;Baldwin, J. E., Magnus, P. D., Ed.; Elsevier Science Ltd:  Oxford; 1994; Vol. 12, pp 41−130. (d) Gais, H.J. InEnzyme Catalysis inOrganic Synthesis; Drauz, K., Waldmann, H., Ed.; VCH:  Weinheim; 1995; Vol. 1; pp 165−261. (e) Procter, G.Asymmetric Synthesis; Oxford University Press:  Oxford; 1996; p 215. (f) Gais, H.J.; Lukas, K. L. InBiocatalysts forFine Chemicals Synthesis; Roberts, S. M., Ed.; Wiley:  Chichester, 1999; Chapter 1:1.1. (g) Bornscheuer, U. T.; Kazlauskas, R. J.Hydrolases inOrganic Synthesis−Regio- and Stereoselective Biotransformations; Wiley-VCH:  Weinheim, 1999.

2. Asymmetric synthesis of a lignan lactone from a Meso anhydride

3. An efficient synthesis of a key intermediate for optically active 5,6--carbapenem antibiotics

4. An asymmetric synthesis of 2,4-dimethylvalerolactone and mevalonolactone using chiral binaphtyldiamine derivatives

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