Abstract
Chemical equations presented. An efficient and unprecedented organocatalytic reaction of γ-nitroketones with α,β-unsaturated aldehydes to give polyfunctionalized [4.4.0] bicyclic skeletons was developed. The diphenylprolinol silyl ether mediated nitro-Michael/Aldol reaction afforded the hexa-substituted decalin carboaldehydes with excellent diastereo- and enantioselectivity (up to >99:1 dr and >99% ee) via a formal [4 + 2] carbocyclization process.
| Original language | English |
|---|---|
| Pages (from-to) | 2200-2203 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 13 |
| Issue number | 9 |
| DOIs | |
| Publication status | Published - 2011 May 6 |
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ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
Cite this
Organocatalytic synthesis of multiple substituted b[4.4.0]decalin system. / Anwar, Shaik; Chang, Hui Ju; Chen, Kwunmin.
In: Organic Letters, Vol. 13, No. 9, 06.05.2011, p. 2200-2203.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Organocatalytic synthesis of multiple substituted b[4.4.0]decalin system
AU - Anwar, Shaik
AU - Chang, Hui Ju
AU - Chen, Kwunmin
PY - 2011/5/6
Y1 - 2011/5/6
N2 - Chemical equations presented. An efficient and unprecedented organocatalytic reaction of γ-nitroketones with α,β-unsaturated aldehydes to give polyfunctionalized [4.4.0] bicyclic skeletons was developed. The diphenylprolinol silyl ether mediated nitro-Michael/Aldol reaction afforded the hexa-substituted decalin carboaldehydes with excellent diastereo- and enantioselectivity (up to >99:1 dr and >99% ee) via a formal [4 + 2] carbocyclization process.
AB - Chemical equations presented. An efficient and unprecedented organocatalytic reaction of γ-nitroketones with α,β-unsaturated aldehydes to give polyfunctionalized [4.4.0] bicyclic skeletons was developed. The diphenylprolinol silyl ether mediated nitro-Michael/Aldol reaction afforded the hexa-substituted decalin carboaldehydes with excellent diastereo- and enantioselectivity (up to >99:1 dr and >99% ee) via a formal [4 + 2] carbocyclization process.
UR - http://www.scopus.com/inward/record.url?scp=79955599615&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=79955599615&partnerID=8YFLogxK
U2 - 10.1021/ol200424x
DO - 10.1021/ol200424x
M3 - Article
C2 - 21476516
AN - SCOPUS:79955599615
VL - 13
SP - 2200
EP - 2203
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 9
ER -