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 language | English |
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Pages (from-to) | 2066-2074 |
Number of pages | 9 |
Journal | European Journal of Organic Chemistry |
Volume | 2015 |
Issue number | 9 |
DOIs | |
Publication status | Published - 2015 Mar |
Keywords
- Alkaloids
- Carbocycles
- Domino reactions
- Enones
- Michael addition
- Organocatalysis
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry