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 |
|---|---|
| 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 |
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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 journal › Article
}
TY - JOUR
T1 - Asymmetric organocatalytic synthesis of highly substituted cyclohexenols by domino double-michael reactions of 1-hydroxy-1,4-dien-3-ones and 2-alkylidenemalononitriles
AU - Jang, Yeong Jiunn
AU - Chen, Yu Shan
AU - Lee, Chia Jui
AU - Chen, Chi Han
AU - Reddy, Ganapuram Madhusudhan
AU - Ko, Chi Ting
AU - Lin, Wenwei
PY - 2015/3
Y1 - 2015/3
N2 - 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).
AB - 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).
KW - Alkaloids
KW - Carbocycles
KW - Domino reactions
KW - Enones
KW - Michael addition
KW - Organocatalysis
UR - http://www.scopus.com/inward/record.url?scp=85027935988&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85027935988&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201403677
DO - 10.1002/ejoc.201403677
M3 - Article
AN - SCOPUS:85027935988
VL - 2015
SP - 2066
EP - 2074
JO - Annalen der Pharmacie
JF - Annalen der Pharmacie
SN - 0075-4617
IS - 9
ER -