Stereoselective allylation reactions of acyclic and chiral α-amino-β-hydroxy aldehydes
作者: In-Soo MyeongYong-Taek LeeSang-Hyun LeeChangyoung JungJin-Seok KimSeok-Hwi ParkJihun KangSeung-Jong LeeIn-Hae YeWon-Hun Ham
作者单位: 1School of Pharmacy, Sungkyunkwan University, Seobu-ro 2066, Suwon-si, Gyeonggi-do 16419, Republic of Korea
刊名: Tetrahedron: Asymmetry, 2017, Vol.28 (8), pp.1053-1060
来源数据库: Elsevier Journal
DOI: 10.1016/j.tetasy.2017.07.002
原始语种摘要: Abstract(#br)Stereoselective allylation reactions of acyclic and chiral α-amino-β-hydroxy aldehydes affording chiral β-amino-α,γ-diols are described. Several Lewis acids (BF 3 ·OEt 2 , SnCl 4 , TiCl 4 , ZnCl 2 , and MgBr 2 ·OEt 2 ) were employed to mediate the allylation reactions. The reactions of anti -α-NHCbz-β-OTBS substrates mediated by SnCl 4 afforded syn -selective products. The same reaction conditions also gave satisfactory results for the reactions of syn -α-NHCbz-β-OTBS substrates. The mechanism involves α-chelation between the amido group and aldehyde oxygen.
全文获取路径: Elsevier  (合作)
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来源刊物:
影响因子:2.115 (2012)

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关键词翻译
关键词翻译
  • amino 氨基
  • allylation 烯丙基化
  • aldehydes 
  • chiral 手性的
  • acyclic 非周期的
  • hydroxy 羟基