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Asymmetric synthesis of arylglycines
Abstract
The asymmetric synthesis of several arylglycines is discussed. Several methods for the coupling of an aromatic group to the chiral bromoglycinates (171, 172) were developed. It was found that the cuprate and Friedel-Crafts couplings provided the desired aryl-coupled glycinates in the greatest yield with excellent selectivity. An oxidative protocol was employed to unmask the oxazinone chiral auxiliary which provided the desired free α-amino acids. A reductive deprotection method was also employed in two unique cases which efficiently gave the arylglycine products. The % ee's ranged from 82 to 94 %. This methodology was further utilized in an approach to the asymmetric synthesis of the bis-arylglycine, actinoidic acid. This study explored the scope of the Stille biphenyl cross-coupling reaction and produced methodology for the synthesis of biphenyl amino acid precursors.
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Citations
Cited by
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Maruoka, K., & Ooi, T. (2003) · Chemical Reviews · doi:10.1021/cr020020e · Cited by 834
Cabré, A., Verdaguer, X., & Riera, A. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00496 · Cited by 477
A Highly Enantioselective Amino Acid-Catalyzed Route to Functionalized α-Amino Acids
Córdova, A., Notz, W., Zhong, G., Betancort, J. M., & Barbas, C. F. (2002) · Journal of the American Chemical Society · doi:10.1021/ja017270h · Cited by 425
Umpolung reactivity in amide and peptide synthesis
Shen, B., Makley, D. M., & Johnston, J. N. (2010) · Nature · doi:10.1038/nature09125 · Cited by 318
Petasis, N. A., & Zavialov, I. A. (1998) · Journal of the American Chemical Society · doi:10.1021/ja981075u · Cited by 309
Metadata
- Authors
- Williams, R. M., & Hendrix, J. A.
- Venue
- Chemical Reviews
- Publisher
- American Chemical Society (ACS)
- Published
- 1992-07-01
- Volume
- 92
- Issue
- 5
- Pages
- 889-917
- ISSN
- 0009-2665 (ISSN-L)
- 1520-6890
- OpenAlex
- W2175353266
- Cited by
- 338
- References
- 0
- FWCI
- 5.88
- Type
- journal article
- Language
- en
- Open access
- closed
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