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
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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