Asymmetric organocatalytic synthesis of highly substituted cyclohexenols by domino double-michael reactions of 1-hydroxy-1,4-dien-3-ones and 2-alkylidenemalononitriles

Yeong Jiunn Jang, Yu Shan Chen, Chia Jui Lee, Chi Han Chen, Ganapuram Madhusudhan Reddy, Chi Ting Ko, Wenwei Lin

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

A facile asymmetric synthetic protocol to afford 2,6-disubstituted 4-hydroxy-3-oxocyclohex-3-ene-1,1-dicarbonitriles has been developed through the domino double-Michael addition of 1,5-disubstituted 1-hydroxy-1,4-dien-3-ones to 2-alkylidenemalononitriles using quinine as the catalyst. This simple organocatalytic domino process provides access to various highly functionalized chiral 4-hydroxy-3-oxocyclohex-3-enes, which are the rarely reported chiral diketo cyclohexane analogues, in moderate-to-good yields and enantioselectivities and with excellent diastereoselectivities (>25:1 dr). An effective asymmetric organocatalytic synthesis of polysubstituted cyclohexenes from 1-hydroxy-1,4-dien-3-ones and 2-alkylidenemalononitriles by a domino double-Michael reaction sequence using quinine as catalyst has been achieved. The products were obtained in moderate-to-good yields (up to 96) and enantioselectivities (up to 92 ee).

Original languageEnglish
Pages (from-to)2066-2074
Number of pages9
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number9
DOIs
Publication statusPublished - 2015 Mar

Fingerprint

Michael reaction
Quinine
Enantioselectivity
Cyclohexenes
catalysts
Catalysts
synthesis
cyclohexane
analogs
products
Cyclohexane

Keywords

  • Alkaloids
  • Carbocycles
  • Domino reactions
  • Enones
  • Michael addition
  • Organocatalysis

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Asymmetric organocatalytic synthesis of highly substituted cyclohexenols by domino double-michael reactions of 1-hydroxy-1,4-dien-3-ones and 2-alkylidenemalononitriles. / Jang, Yeong Jiunn; Chen, Yu Shan; Lee, Chia Jui; Chen, Chi Han; Reddy, Ganapuram Madhusudhan; Ko, Chi Ting; Lin, Wenwei.

In: European Journal of Organic Chemistry, Vol. 2015, No. 9, 03.2015, p. 2066-2074.

Research output: Contribution to journalArticle

Jang, Yeong Jiunn ; Chen, Yu Shan ; Lee, Chia Jui ; Chen, Chi Han ; Reddy, Ganapuram Madhusudhan ; Ko, Chi Ting ; Lin, Wenwei. / Asymmetric organocatalytic synthesis of highly substituted cyclohexenols by domino double-michael reactions of 1-hydroxy-1,4-dien-3-ones and 2-alkylidenemalononitriles. In: European Journal of Organic Chemistry. 2015 ; Vol. 2015, No. 9. pp. 2066-2074.
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