Cyclic α-Amino Acids via Enantioselective Metal-Catalyzed Cascade Reactions of Dienamides in Supercritical Carbon Dioxide

Euneace Teoh; W. Roy Jackson; Andrea J. Robinson

doi:10.1071/CH04219

RESEARCH ARTICLE

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Cyclic α-Amino Acids via Enantioselective Metal-Catalyzed Cascade Reactions of Dienamides in Supercritical Carbon Dioxide

Euneace Teoh ^A , W. Roy Jackson ^A and Andrea J. Robinson ^A ^B

+ Author Affiliations

- Author Affiliations

^A Centre for Green Chemistry and School of Chemistry, Monash University, Melbourne VIC 3800, Australia.

^B Corresponding author. Email: Andrea.Robinson@sci.monash.edu.au

Australian Journal of Chemistry 58(1) 63-65 https://doi.org/10.1071/CH04219
Submitted: 22 September 2004 Accepted: 2 December 2004 Published: 1 January 2005

Abstract

Highly enantioselective conversion of dienamides into cyclic α-amino acids can be achieved by a single-pot, tandem hydrogenation–hydroformylation–cyclization–elimination sequence using a single catalyst and supercritical carbon dioxide (scCO₂) as the reaction solvent at total pressures significantly lower than those previously reported for related hydrogenation and hydroformylation reactions.

Acknowledgments

We thank Monash University and the Centre for Green Chemistry for provision of a postgraduate award (to E.T.), the Australian Research Council for its financial support of our research, Johnson Matthey Pty Ltd for a loan of rhodium, and Dr Ulf Kreher, Associate Professor Andrew Smallridge, and Miss Kylie Blake for assistance with scCO₂ reactions.

References

Cyclic α-Amino Acids via Enantioselective Metal-Catalyzed Cascade Reactions of Dienamides in Supercritical Carbon Dioxide

Abstract

Acknowledgments

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