Regio- and π-facial selective Lewis acid interceded Diels-Alder reactions of α-dienyl-β-lactams: an indepth analysis

Gaurav Bhargava, Amit Anand, Mohinder P. Mahajan, Takao Saito, Ken Sakai, Chitrani Medhi

研究成果: ジャーナルへの寄稿記事

17 引用 (Scopus)

抄録

The regio-, diastereo-, and π-facial selective Lewis acid mediated Diels-Alder reactions of cis/trans-3-butadienyl-2-azetidinones with unsymmetrical dienophiles viz. methyl acrylate, dimethyl fumarate, and acrolein leading to the synthesis of diastereomerically pure and biologically potent 1,3,4-trisubstituted-2-azetidinones are reported. Theoretical calculations at HF/6-31G** and 6-31G**/DFT levels have been performed to support the observed π-facial selectivity. The formation of diastereomerically pure 'endo' adducts is supported by the X-ray diffraction studies.

元の言語英語
ページ(範囲)6801-6808
ページ数8
ジャーナルTetrahedron
64
発行部数28
DOI
出版物ステータス出版済み - 7 7 2008

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Lactams
Lewis Acids
Cycloaddition Reaction
Acrolein
Discrete Fourier transforms
X-Ray Diffraction
X ray diffraction
2-azetidinone
Dimethyl Fumarate
methyl acrylate

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

これを引用

Regio- and π-facial selective Lewis acid interceded Diels-Alder reactions of α-dienyl-β-lactams : an indepth analysis. / Bhargava, Gaurav; Anand, Amit; Mahajan, Mohinder P.; Saito, Takao; Sakai, Ken; Medhi, Chitrani.

:: Tetrahedron, 巻 64, 番号 28, 07.07.2008, p. 6801-6808.

研究成果: ジャーナルへの寄稿記事

Bhargava, Gaurav ; Anand, Amit ; Mahajan, Mohinder P. ; Saito, Takao ; Sakai, Ken ; Medhi, Chitrani. / Regio- and π-facial selective Lewis acid interceded Diels-Alder reactions of α-dienyl-β-lactams : an indepth analysis. :: Tetrahedron. 2008 ; 巻 64, 番号 28. pp. 6801-6808.
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