Microwave assisted Wolff rearrangement: A facile method for the synthesis of Fmoc-β-amino acids

被引:0
|
作者
Basanagoud S. Patil
Ganga-Ramu Vasanthakumar
Vommina V. Suresh Babu
机构
[1] Bangalore University,Department of Studies in Chemistry, Central College Campus
来源
关键词
β-amino acids; microwave irradiation; -Fmoc-α-aminodiazoketones; Wolff rearrangement;
D O I
暂无
中图分类号
学科分类号
摘要
The Wolff rearrangement of α-diazoketones, derived from Fmoc-α-amino acids, under no base conditions on exposure to microwave irradiation for 40 to 60 sec to Fmoc-β-amino acids with retention of configuration in good yield (91–95%) is described.
引用
收藏
页码:231 / 233
页数:2
相关论文
共 50 条
  • [1] Microwave assisted Wolff rearrangement:: A facile method for the synthesis of Fmoc-β-amino acids
    Patil, BS
    Vasanthakumar, GR
    Babu, VVS
    LETTERS IN PEPTIDE SCIENCE, 2002, 9 (4-5): : 231 - 233
  • [2] Synthesis of Fmoc-β-homoamino acids by ultrasound-promoted Wolff rearrangement
    Müller, A
    Vogt, C
    Sewald, N
    SYNTHESIS-STUTTGART, 1998, (06): : 837 - 841
  • [3] Facile synthesis of glycosylated Fmoc amino acid building blocks assisted by microwave irradiation
    Yao, Nianhuan
    Fung, Gabriel
    Malekan, Hamed
    Ye, Long
    Kurth, Mark J.
    Lam, Kit S.
    CARBOHYDRATE RESEARCH, 2010, 345 (15) : 2277 - 2281
  • [4] Synthesis of Fmoc-/Boc-/Z-β-amino acids via Arndt-Eistert homologation of Fmoc-/Boc-/Z-α-amino acids employing BOP and PyBOP
    Vasanthakumar, GR
    Buba, VVS
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2003, 42 (07): : 1691 - 1695
  • [5] Facile synthesis of Fmoc-N-methylated α- and β-amino acids
    Govender, T
    Arvidsson, PI
    TETRAHEDRON LETTERS, 2006, 47 (11) : 1691 - 1694
  • [6] Wolff rearrangement of Nα-protected α-aminodiazoketones in presence of substituted phenol as a method for the synthesis of 2,4,5-trichlorophenyl esters of Fmoc-/Boc-/Z-β-homoamino acids
    Gopi, HN
    Ananda, K
    Babu, VVS
    PROTEIN AND PEPTIDE LETTERS, 2000, 7 (01): : 33 - 36
  • [7] Syntheses of nucleoside derivatives containing Fmoc- or trityl-protected amino acids
    Guo, H
    Zou, WX
    Ji, Q
    Ma, YX
    Meng, JB
    CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2005, 21 (04) : 447 - 451
  • [8] Fmoc/Trt amino acids: comparison to Fmoc/tBu amino acids in peptide synthesis
    Barlos, K
    Gatos, D
    Koutsogianni, S
    JOURNAL OF PEPTIDE RESEARCH, 1998, 51 (03): : 194 - 200
  • [9] Benzotriazole Reagents for the Syntheses of Fmoc-, Boc-, and Alloc-Protected Amino Acids
    Ibrahim, Tarek S.
    Tala, Srinivasa R.
    El-Feky, Said A.
    Abdel-Samii, Zakaria K.
    Katritzky, Alan R.
    SYNLETT, 2011, (14) : 2013 - 2016
  • [10] Convenient and simple synthesis of N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-(Fmoc) protected β-amino acids (=homo-α-amino acids) employing Fmoc-α-amino acids and dicyclohexylcarbodiimide(DCC) mixtures
    Ananda, K
    Babu, VVS
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1999, 38 (04): : 418 - 423