Abstract
A simple and convenient strategy was developed to synthesize a new class of pyrrolidinyl-camphor based bifunctional organocatalysts possessing varying functional linkers. Catalytic screening of these camphor-pyrrolidine linked derivatives for asymmetric Michael reaction of cyclohexanone with β-nitrostyrene was carried out. Various aryl- and heteroaryl-nitroolefins, ketones as well as aldehydes gave the corresponding Michael adducts in high chemical yields (up to 95%) and exceptionally high diastereo-(syn/anti up to 99:1) and enantioselectivity (up to 95%) using catalyst 6 under solvent-free conditions.
| Original language | English |
|---|---|
| Pages (from-to) | 1171-1177 |
| Number of pages | 7 |
| Journal | Tetrahedron |
| Volume | 67 |
| Issue number | 6 |
| DOIs | |
| Publication status | Published - 2011 Feb 11 |
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Keywords
- Camphor
- Linker
- Michael addition
- Nitroolefins
- Organocatalysis
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
Cite this
Pyrrolidine-linker-camphor assembly : Bifunctional organocatalysts for efficient Michael addition of cyclohexanone to nitroolefins under neat conditions. / Anwar, Shaik; Lee, Pei Hsun; Chou, Tsai Yung; Chang, Chihliang; Chen, Kwunmin.
In: Tetrahedron, Vol. 67, No. 6, 11.02.2011, p. 1171-1177.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Pyrrolidine-linker-camphor assembly
T2 - Bifunctional organocatalysts for efficient Michael addition of cyclohexanone to nitroolefins under neat conditions
AU - Anwar, Shaik
AU - Lee, Pei Hsun
AU - Chou, Tsai Yung
AU - Chang, Chihliang
AU - Chen, Kwunmin
PY - 2011/2/11
Y1 - 2011/2/11
N2 - A simple and convenient strategy was developed to synthesize a new class of pyrrolidinyl-camphor based bifunctional organocatalysts possessing varying functional linkers. Catalytic screening of these camphor-pyrrolidine linked derivatives for asymmetric Michael reaction of cyclohexanone with β-nitrostyrene was carried out. Various aryl- and heteroaryl-nitroolefins, ketones as well as aldehydes gave the corresponding Michael adducts in high chemical yields (up to 95%) and exceptionally high diastereo-(syn/anti up to 99:1) and enantioselectivity (up to 95%) using catalyst 6 under solvent-free conditions.
AB - A simple and convenient strategy was developed to synthesize a new class of pyrrolidinyl-camphor based bifunctional organocatalysts possessing varying functional linkers. Catalytic screening of these camphor-pyrrolidine linked derivatives for asymmetric Michael reaction of cyclohexanone with β-nitrostyrene was carried out. Various aryl- and heteroaryl-nitroolefins, ketones as well as aldehydes gave the corresponding Michael adducts in high chemical yields (up to 95%) and exceptionally high diastereo-(syn/anti up to 99:1) and enantioselectivity (up to 95%) using catalyst 6 under solvent-free conditions.
KW - Camphor
KW - Linker
KW - Michael addition
KW - Nitroolefins
KW - Organocatalysis
UR - http://www.scopus.com/inward/record.url?scp=78751570918&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=78751570918&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2010.11.093
DO - 10.1016/j.tet.2010.11.093
M3 - Article
AN - SCOPUS:78751570918
VL - 67
SP - 1171
EP - 1177
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 6
ER -