The Enantioselective Synthesis of β??Amino Acids, their α??hydroxy derivatives, and the N??terminal components of bestatin and microginin
CW Jefford, J McNulty, ZH Lu…
Index: Jefford, Charles W.; McNulty, James; Lu, Zhi-Hui; Wang, Jian Bo Helvetica Chimica Acta, 1996 , vol. 79, # 4 p. 1203 - 1216
Full Text: HTML
Citation Number: 51
Abstract
Abstract L-Aspartic acid by tosylation, anhydride formation, and reduction with NaBH 4 was converted into (3S)-3-(tosylamino) butan-4-olide (8; Scheme 1). Tretment of 8 with ethanolic trimethylsilyl iodide gave the N-protected deoxy-iodo-β-homoserine ethyl ester 9. The latter, on successive nucleophilic displacement with lithium dialkyl-cuprates ([RIGHTWARDS ARROW] 10a–e), alkaline hydrolysis ([RIGHTWARDS ARROW] 11a–e), and reductive ...
Related Articles:
[Juaristi, Eusebio; Escalante, Jaime; Lamatsch, Bernd; Seebach, Dieter Journal of Organic Chemistry, 1992 , vol. 57, # 8 p. 2396 - 2398]
Homochiral lithium amides for the asymmetric synthesis of β-amino acids
[Davies, Stephen G.; Garrido, Narciso M.; Kruchinin, Dennis; Ichihara, Osamu; Kotchie, Luke J.; Price, Paul D.; Mortimer, Anne J. Price; Russell, Angela J.; Smith, Andrew D. Tetrahedron Asymmetry, 2006 , vol. 17, # 12 p. 1793 - 1811]
Efficient EPC synthesis of β??aminobutanoic acid
[Gmeiner, Peter Liebigs Annalen der Chemie, 1991 , # 5 p. 501 - 502]
Parallel synthesis of homochiral β-amino acids
[Davies, Stephen G.; Mulvaney, Andrew W.; Russell, Angela J.; Smith, Andrew D. Tetrahedron Asymmetry, 2007 , vol. 18, # 13 p. 1554 - 1566]
[Li, Xiang-Guo; Laehitie, Maria; Kanerva, Liisa T. Tetrahedron Asymmetry, 2008 , vol. 19, # 15 p. 1857 - 1861]