Abstract
A cinchona alkaloid-catalyzed enantioselective method has been developed for the synthesis of densely functionalized cyclohexanone derivatives with excellent diastereoselectivities and good enantioselectivities [diastereomeric ratio (dr) >95:5 and an enantiomeric excess (ee) value up to 86%]. The products have an all-carbon quaternary center that contains both a cyano and ester group flanked by two vicinal tertiary stereocenters. By using a one-pot procedure, the tautomeric products were then transformed into the corresponding pyrazoles, which were obtained as single isomers in good yields. A quinine-catalyzed enantioselective method has been reported to generate polysubstituted cyclohexenes that have an all-carbon quaternary center. The resulting isomeric product mixtures were easily converted into the corresponding pyrazoles through a one-pot procedure.
| Original language | English |
|---|---|
| Pages (from-to) | 5254-5265 |
| Number of pages | 12 |
| Journal | European Journal of Organic Chemistry |
| Volume | 2015 |
| Issue number | 23 |
| DOIs | |
| Publication status | Published - 2015 Aug 1 |
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Keywords
- Asymmetric synthesis
- Carbocycles
- Domino reactions
- Enones
- Michael addition
- Organocatalysis
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
Cite this
An Enantioselective Synthesis of Substituted Cyclohexanone Derivatives with an All-Carbon Quaternary Stereocenter by Using an Organocatalytic Asymmetric Domino Double Michael Addition. / Chen, Chi Han; Ko, Chi Ting; Reddy, Ganapuram Madhusudhan; Lee, Chia Jui; Lin, Wenwei.
In: European Journal of Organic Chemistry, Vol. 2015, No. 23, 01.08.2015, p. 5254-5265.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - An Enantioselective Synthesis of Substituted Cyclohexanone Derivatives with an All-Carbon Quaternary Stereocenter by Using an Organocatalytic Asymmetric Domino Double Michael Addition
AU - Chen, Chi Han
AU - Ko, Chi Ting
AU - Reddy, Ganapuram Madhusudhan
AU - Lee, Chia Jui
AU - Lin, Wenwei
PY - 2015/8/1
Y1 - 2015/8/1
N2 - A cinchona alkaloid-catalyzed enantioselective method has been developed for the synthesis of densely functionalized cyclohexanone derivatives with excellent diastereoselectivities and good enantioselectivities [diastereomeric ratio (dr) >95:5 and an enantiomeric excess (ee) value up to 86%]. The products have an all-carbon quaternary center that contains both a cyano and ester group flanked by two vicinal tertiary stereocenters. By using a one-pot procedure, the tautomeric products were then transformed into the corresponding pyrazoles, which were obtained as single isomers in good yields. A quinine-catalyzed enantioselective method has been reported to generate polysubstituted cyclohexenes that have an all-carbon quaternary center. The resulting isomeric product mixtures were easily converted into the corresponding pyrazoles through a one-pot procedure.
AB - A cinchona alkaloid-catalyzed enantioselective method has been developed for the synthesis of densely functionalized cyclohexanone derivatives with excellent diastereoselectivities and good enantioselectivities [diastereomeric ratio (dr) >95:5 and an enantiomeric excess (ee) value up to 86%]. The products have an all-carbon quaternary center that contains both a cyano and ester group flanked by two vicinal tertiary stereocenters. By using a one-pot procedure, the tautomeric products were then transformed into the corresponding pyrazoles, which were obtained as single isomers in good yields. A quinine-catalyzed enantioselective method has been reported to generate polysubstituted cyclohexenes that have an all-carbon quaternary center. The resulting isomeric product mixtures were easily converted into the corresponding pyrazoles through a one-pot procedure.
KW - Asymmetric synthesis
KW - Carbocycles
KW - Domino reactions
KW - Enones
KW - Michael addition
KW - Organocatalysis
UR - http://www.scopus.com/inward/record.url?scp=84938750405&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84938750405&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201500524
DO - 10.1002/ejoc.201500524
M3 - Article
AN - SCOPUS:84938750405
VL - 2015
SP - 5254
EP - 5265
JO - Annalen der Pharmacie
JF - Annalen der Pharmacie
SN - 0075-4617
IS - 23
ER -