Diastereoselective Synthesis of Functionalized Angularly-Fused Tetracycles via an Organocatalytic Quadruple Reaction Sequence

Fu Jie Chang, Ramani Gurubrahamam, Kwunmin Chen

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

An efficient diastereoselective strategy to access complex structural tetracycles was described through an organocascade quadruple reaction sequence between (E)-2-(3-arylallylidene)-1H-indene-1,3(2H)-diones and β-keto esters. The reaction proceeded through remote 1,6-addition followed by sequential 1,4-addition and aldol/aldol reactions to generate angularly-fused carbocyclic motifs with favourable to excellent yields (up to 94%) and diastereoselectivities (up to >20:1 dr). An enantioselective organocascade approach was attempted to yield densely functionalized tetracycles containing seven chiral centres including a quaternary centre. (Figure presented.).

Original languageEnglish
Pages (from-to)1277-1282
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume359
Issue number8
DOIs
Publication statusPublished - 2017 Jan 1

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Esters
3-hydroxybutanal
1,3-indandione

Keywords

  • Michael reaction
  • indane-1,3-diones
  • organocatalysis
  • quadruple reaction sequence

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Diastereoselective Synthesis of Functionalized Angularly-Fused Tetracycles via an Organocatalytic Quadruple Reaction Sequence. / Chang, Fu Jie; Gurubrahamam, Ramani; Chen, Kwunmin.

In: Advanced Synthesis and Catalysis, Vol. 359, No. 8, 01.01.2017, p. 1277-1282.

Research output: Contribution to journalArticle

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