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DOI: 10.1055/s-0043-1775436
Synthetic Applications of Amino Acid Derived Aldehydes in Asymmetric Hydroxylation Reactions Using Nitrosobenzene
We gratefully acknowledge the University Grants Commission, New Delhi, India, for financial support in the form of a Junior Research Fellowship (JRF) Sudeep Dhillon (Ref. No. 114/(CSIR UGC NET JUNE)).
Abstract
This review highlights the proline-catalyzed asymmetric α-hydroxylation of aldehydes derived from amino acids. This reaction provides a robust method for introducing a hydroxyl group at the α-position of the aldehyde with high stereocontrol. The stereochemical outcome of the hydroxylation is primarily governed by the chiral environment of the proline catalyst and is further influenced by the pre-existing chiral center within the substrate. Post-hydroxylation, the aldehyde intermediates can be readily transformed into alcohols or olefins, depending on the synthetic requirements. We explore the utility of amino acid derived aldehydes, such as those obtained from l-glutamic acid, phenylalanine, proline, and l-aspartic acid, in the context of asymmetric synthesis. The scope of this methodology extends to the efficient construction of various natural products and bioactive compounds, highlighting its significance in modern organic synthesis.
1 Introduction
2 Mechanistic Overview of the Proline-Catalyzed Asymmetric α-Hydroxylation of Aldehydes
3 Review of the Proline-Catalyzed Asymmetric α-Hydroxylation of Aldehydes
4 Current Overview and Future Prospective
5 Conclusion
Publication History
Received: 09 September 2024
Accepted after revision: 09 December 2024
Article published online:
27 January 2025
© 2025. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
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