Abstract
Practical and convenient synthetic routes have been developed for the synthesis of a new class of pyrrolidinyl-camphor derivatives (7a-h). These novel compounds were screened as catalysts for the direct Michael addition of symmetrical αα-disubstituted aldehydes to β-nitroalkenes. When this asymmetric transformation was cata-lyzed by organocatalyst 7f, the desired Michael adducts were obtained in high chemical yields, with high to excellent stereoselectivities (up to 98:2 diaste-reomeric ratio (d.r.) and 99% enantiomeric excess (ee)). The scope of the catalytic system was expanded to encompass various aldehydes and ketones as the donor sources. The synthetic application was demonstrated by the synthesis of a tetrasubstituted-cyclohexane derivative from (S)-citronellal, with high stereoselectivity.
| Original language | English |
|---|---|
| Pages (from-to) | 7030-7038 |
| Number of pages | 9 |
| Journal | Chemistry - A European Journal |
| Volume | 16 |
| Issue number | 23 |
| DOIs | |
| Publication status | Published - 2010 Jun 18 |
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Keywords
- Camphor
- Citronellal
- Michael addition
- Nitroalkenes
- Organocatalysis
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
- Organic Chemistry
Cite this
Pyrrolidinyl-camphor derivatives as a new class of organocatalyst for direct asymmetric Michael addition of aldehydes and ketones to β-nitroalkenes. / Ting, Ying Fang; Chang, Chihliang; Reddy, Raju Jannapu; Magar, Dhananjay R.; Chen, Kwunmin.
In: Chemistry - A European Journal, Vol. 16, No. 23, 18.06.2010, p. 7030-7038.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Pyrrolidinyl-camphor derivatives as a new class of organocatalyst for direct asymmetric Michael addition of aldehydes and ketones to β-nitroalkenes
AU - Ting, Ying Fang
AU - Chang, Chihliang
AU - Reddy, Raju Jannapu
AU - Magar, Dhananjay R.
AU - Chen, Kwunmin
PY - 2010/6/18
Y1 - 2010/6/18
N2 - Practical and convenient synthetic routes have been developed for the synthesis of a new class of pyrrolidinyl-camphor derivatives (7a-h). These novel compounds were screened as catalysts for the direct Michael addition of symmetrical αα-disubstituted aldehydes to β-nitroalkenes. When this asymmetric transformation was cata-lyzed by organocatalyst 7f, the desired Michael adducts were obtained in high chemical yields, with high to excellent stereoselectivities (up to 98:2 diaste-reomeric ratio (d.r.) and 99% enantiomeric excess (ee)). The scope of the catalytic system was expanded to encompass various aldehydes and ketones as the donor sources. The synthetic application was demonstrated by the synthesis of a tetrasubstituted-cyclohexane derivative from (S)-citronellal, with high stereoselectivity.
AB - Practical and convenient synthetic routes have been developed for the synthesis of a new class of pyrrolidinyl-camphor derivatives (7a-h). These novel compounds were screened as catalysts for the direct Michael addition of symmetrical αα-disubstituted aldehydes to β-nitroalkenes. When this asymmetric transformation was cata-lyzed by organocatalyst 7f, the desired Michael adducts were obtained in high chemical yields, with high to excellent stereoselectivities (up to 98:2 diaste-reomeric ratio (d.r.) and 99% enantiomeric excess (ee)). The scope of the catalytic system was expanded to encompass various aldehydes and ketones as the donor sources. The synthetic application was demonstrated by the synthesis of a tetrasubstituted-cyclohexane derivative from (S)-citronellal, with high stereoselectivity.
KW - Camphor
KW - Citronellal
KW - Michael addition
KW - Nitroalkenes
KW - Organocatalysis
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UR - http://www.scopus.com/inward/citedby.url?scp=77953563112&partnerID=8YFLogxK
U2 - 10.1002/chem.201000483
DO - 10.1002/chem.201000483
M3 - Article
C2 - 20455225
AN - SCOPUS:77953563112
VL - 16
SP - 7030
EP - 7038
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 23
ER -