Organocatalytic Enantioselective Synthesis of Tetrahydrofluoren-9-ones via Vinylogous Michael Addition/Henry Reaction Cascade of 1,3-Indandione-Derived Pronucleophiles

Lennart Möhlmann, Geng Hua Chang, G. Madhusudhan Reddy, Chia Jui Lee, Wenwei Lin

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

An unprecedented organocatalytic enantioselective vinylogous Michael addition/Henry cyclization cascade is presented for the synthesis of highly substituted tetrahydrofluoren-9-ones 3 employing novel 1,3-indandione-derived pronucleophiles 1a-g and nitroalkenes 2. Following a very simple protocol, a wide range of products were obtained in good to excellent yields and with excellent enantioinduction (43-98% yield, up to 98% ee). The reaction proceeded with excellent diastereocontrol despite the simultaneous generation of four stereogenic centers. Surprisingly, when 2-(1-phenylethylidene)-1H-indandione (1h) was used as a pronucleophile, no cyclization was observed, and only Michael addition adducts 4a-x were furnished in very good yields and excellent enantioselectivities. (Chemical Equation Presented).

Original languageEnglish
Pages (from-to)688-691
Number of pages4
JournalOrganic Letters
Volume18
Issue number4
DOIs
Publication statusPublished - 2016 Feb 19

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Addition reactions
Cyclization
cascades
Enantioselectivity
synthesis
adducts
products
1,3-indandione

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Organocatalytic Enantioselective Synthesis of Tetrahydrofluoren-9-ones via Vinylogous Michael Addition/Henry Reaction Cascade of 1,3-Indandione-Derived Pronucleophiles. / Möhlmann, Lennart; Chang, Geng Hua; Madhusudhan Reddy, G.; Lee, Chia Jui; Lin, Wenwei.

In: Organic Letters, Vol. 18, No. 4, 19.02.2016, p. 688-691.

Research output: Contribution to journalArticle

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AB - An unprecedented organocatalytic enantioselective vinylogous Michael addition/Henry cyclization cascade is presented for the synthesis of highly substituted tetrahydrofluoren-9-ones 3 employing novel 1,3-indandione-derived pronucleophiles 1a-g and nitroalkenes 2. Following a very simple protocol, a wide range of products were obtained in good to excellent yields and with excellent enantioinduction (43-98% yield, up to 98% ee). The reaction proceeded with excellent diastereocontrol despite the simultaneous generation of four stereogenic centers. Surprisingly, when 2-(1-phenylethylidene)-1H-indandione (1h) was used as a pronucleophile, no cyclization was observed, and only Michael addition adducts 4a-x were furnished in very good yields and excellent enantioselectivities. (Chemical Equation Presented).

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