Organocascade Synthesis of Bicyclo[3.3.1]nonan-9-ones Initiated by an Unusual 1,6-Addition of Cyclohexanones to (E)-2-(3-Arylallylidene)-1H-indene-1,3(2H)-diones

De Chih Wang, Pin Han Huang, Wan Wun Huang, You Song Cheng, Kwunmin Chen

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

An efficient organocatalytic cascade reaction for the synthesis of the bicyclo[3.3.1]nonan-9-one skeleton is reported. The cascade reaction proceeds smoothly between prochiral 4-substituted cyclohexanones and (E)-2-(3-arylallylidene)-indene-1,3-diones involving a 1,6-/γ-protonation/1,4-addition sequence to construct bicyclic products that contain five stereogenic centers in good to high chemical yields and excellent diastereo- and enantioselectivity (up to >20:1 dr and 97% ee) in the presence of a thioether-linked l-prolinol-camphor-derived organocatalyst at ambient temperature. An interesting organocatalytic three-component triple cascade reaction has been performed to produce a bicyclo[2.2.2]octan-2-one in a favorable chemical yield and stereoselectivity (>19:1 dr and 97% ee) starting from 1,3-indanedione, an enal, and cyclohexenone in the presence of a primary amine organocatalyst. (Figure presented.).

Original languageEnglish
Pages (from-to)3005-3013
Number of pages9
JournalAdvanced Synthesis and Catalysis
Volume359
Issue number17
DOIs
Publication statusPublished - 2017 Sep 4

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Cyclohexanones
Camphor
Stereoselectivity
Enantioselectivity
Protonation
Sulfides
Amines
Temperature
1,3-indandione

Keywords

  • bicyclic compounds
  • cascade reaction
  • enantioselectivity
  • organocatalysis
  • vinylogous process

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Organocascade Synthesis of Bicyclo[3.3.1]nonan-9-ones Initiated by an Unusual 1,6-Addition of Cyclohexanones to (E)-2-(3-Arylallylidene)-1H-indene-1,3(2H)-diones. / Wang, De Chih; Huang, Pin Han; Huang, Wan Wun; Cheng, You Song; Chen, Kwunmin.

In: Advanced Synthesis and Catalysis, Vol. 359, No. 17, 04.09.2017, p. 3005-3013.

Research output: Contribution to journalArticle

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abstract = "An efficient organocatalytic cascade reaction for the synthesis of the bicyclo[3.3.1]nonan-9-one skeleton is reported. The cascade reaction proceeds smoothly between prochiral 4-substituted cyclohexanones and (E)-2-(3-arylallylidene)-indene-1,3-diones involving a 1,6-/γ-protonation/1,4-addition sequence to construct bicyclic products that contain five stereogenic centers in good to high chemical yields and excellent diastereo- and enantioselectivity (up to >20:1 dr and 97{\%} ee) in the presence of a thioether-linked l-prolinol-camphor-derived organocatalyst at ambient temperature. An interesting organocatalytic three-component triple cascade reaction has been performed to produce a bicyclo[2.2.2]octan-2-one in a favorable chemical yield and stereoselectivity (>19:1 dr and 97{\%} ee) starting from 1,3-indanedione, an enal, and cyclohexenone in the presence of a primary amine organocatalyst. (Figure presented.).",
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