A new synthesis of α-arylglycines from aryl boronic acids
作者： Nicos A. Petasis , Andrew Goodman , Ilia A. Zavialov
DOI: 10.1016/S0040-4020(97)01028-4
关键词: Aryl 、 Petasis reaction 、 Suzuki reaction 、 Glyoxylic acid 、 Organic chemistry 、 Glycine 、 Chemistry 、 Adduct 、 Biochemistry 、 Drug discovery
摘要: Abstract Aryl and heteroaryl boronic acids react with the adducts of amines glyoxylic acid to give corresponding α-aryl α-heteroaryl glycine derivatives. Several examples this reaction m - p -substituted aryl as well 3-thienyl, 2-thienyl, 2-furyl, 2-benzo[b]furyl 2-benzo[b]thienyl are described.
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sci-hub.se 参考文章(43)
J.C. Watkins, G.L. Collingridge, Phenylglycine derivatives as antagonists of metabotropic glutamate receptors Trends in Pharmacological Sciences. ,vol. 15, pp. 333- 342 ,(1994) , 10.1016/0165-6147(94)90028-0
David A. Evans, Deborah A. Evrad, Scott D. Rychnovsky, Thomas Früh, William G. Whittingham, Keith M. deVries, A general approach to the asymmetric synthesis of vancomycin-related arylglycines by enolate azidation Tetrahedron Letters. ,vol. 33, pp. 1189- 1192 ,(1992) , 10.1016/S0040-4039(00)91892-6
H. Suenaga, H. Yamamoto, S. Shinkai, Screening of boronic acids for strong inhibition of the hydrolytic activity of α-chymotrypsin and for sugar sensing associated with a large fluorescence change Pure and Applied Chemistry. ,vol. 68, pp. 2179- 2186 ,(1996) , 10.1351/PAC199668112179
A. V. Rama. Rao, Mukund K. Gurjar, K. Laxma. Reddy, A. Srinivasa. Rao, Studies directed toward the synthesis of vancomycin and related cyclic peptides Chemical Reviews. ,vol. 95, pp. 2135- 2167 ,(1995) , 10.1021/CR00038A014
J C J Barna, D H Williams, The Structure and Mode of Action of Glycopeptide Antibiotics of the Vancomycin Group Annual Review of Microbiology. ,vol. 38, pp. 339- 357 ,(1984) , 10.1146/ANNUREV.MI.38.100184.002011
Robert M. Williams, James A. Hendrix, Asymmetric synthesis of arylglycines Journal of Organic Chemistry. ,vol. 55, pp. 3723- 3728 ,(1990) , 10.1021/CR00013A007
D. S. Matteson, Preparation and use of organoboranes in organic synthesis ChemInform. ,vol. 19, pp. 307- 409 ,(2010) , 10.1002/9780470771778.CH3
Akira Suzuki, New synthetic transformations via organoboron compounds Pure and Applied Chemistry. ,vol. 66, pp. 213- 222 ,(1994) , 10.1351/PAC199466020213
Daniel T. W. Chu, Jacob J. Plattner, Leonard Katz, New directions in antibacterial research. Journal of Medicinal Chemistry. ,vol. 39, pp. 3853- 3874 ,(1996) , 10.1021/JM960294S
Dale L. Boger, Robert M. Borzilleri, Seiji Nukui, Synthesis of (R)-(4-Methoxy-3,5-dihydroxyphenyl)glycine Derivatives: The Central Amino Acid of Vancomycin and Related Agents Journal of Organic Chemistry. ,vol. 61, pp. 3561- 3565 ,(1996) , 10.1021/JO960085F