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

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)6801-6808
Number of pages8
JournalTetrahedron
Volume64
Issue number28
DOIs
Publication statusPublished - Jul 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

Cite this

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.

In: Tetrahedron, Vol. 64, No. 28, 07.07.2008, p. 6801-6808.

Research output: Contribution to journalArticle

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. In: Tetrahedron. 2008 ; Vol. 64, No. 28. pp. 6801-6808.
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