Abstract
The synthesis of a large number of β-and β,β-substituted keto esters was successful by the use of the Knoevenagel condensation reaction. The stereoselectivity of these reactions was improved by alteration of various substituent groups. Although there were few examples of complete Z selectivity, the use of tert-butyl acetoacetate with either aromatic or aliphatic aldehydes afforded Z selectivity. The selective reductions of these substituted keto esters was successfully achieved by using a combination of NaBH 4 and CeCl 3·7H 2O or Yb(OTf) 3, which allowed a facile synthesis of a large number of stereochemically pure substituted Morita-Baylis-Hillman adducts, including β,β-substituted adducts.
| Original language | English |
|---|---|
| Pages (from-to) | 450-463 |
| Number of pages | 14 |
| Journal | Canadian Journal of Chemistry |
| Volume | 90 |
| Issue number | 5 |
| DOIs | |
| Publication status | Published - May 1 2012 |
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All Science Journal Classification (ASJC) codes
- Catalysis
- Chemistry(all)
- Organic Chemistry
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Synthesis of β-and β,β-substituted Morita-Baylis-Hillman adducts using a two-step protocol. / MaGee, David I.; Ratshonka, Same; McConaghy, Jessica; Hood, Maggie.
In: Canadian Journal of Chemistry, Vol. 90, No. 5, 01.05.2012, p. 450-463.Research output: Contribution to journal › Article
TY - JOUR
T1 - Synthesis of β-and β,β-substituted Morita-Baylis-Hillman adducts using a two-step protocol
AU - MaGee, David I.
AU - Ratshonka, Same
AU - McConaghy, Jessica
AU - Hood, Maggie
PY - 2012/5/1
Y1 - 2012/5/1
N2 - The synthesis of a large number of β-and β,β-substituted keto esters was successful by the use of the Knoevenagel condensation reaction. The stereoselectivity of these reactions was improved by alteration of various substituent groups. Although there were few examples of complete Z selectivity, the use of tert-butyl acetoacetate with either aromatic or aliphatic aldehydes afforded Z selectivity. The selective reductions of these substituted keto esters was successfully achieved by using a combination of NaBH 4 and CeCl 3·7H 2O or Yb(OTf) 3, which allowed a facile synthesis of a large number of stereochemically pure substituted Morita-Baylis-Hillman adducts, including β,β-substituted adducts.
AB - The synthesis of a large number of β-and β,β-substituted keto esters was successful by the use of the Knoevenagel condensation reaction. The stereoselectivity of these reactions was improved by alteration of various substituent groups. Although there were few examples of complete Z selectivity, the use of tert-butyl acetoacetate with either aromatic or aliphatic aldehydes afforded Z selectivity. The selective reductions of these substituted keto esters was successfully achieved by using a combination of NaBH 4 and CeCl 3·7H 2O or Yb(OTf) 3, which allowed a facile synthesis of a large number of stereochemically pure substituted Morita-Baylis-Hillman adducts, including β,β-substituted adducts.
UR - http://www.scopus.com/inward/record.url?scp=84860517202&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84860517202&partnerID=8YFLogxK
U2 - 10.1139/v2012-017
DO - 10.1139/v2012-017
M3 - Article
VL - 90
SP - 450
EP - 463
JO - Canadian Journal of Chemistry
JF - Canadian Journal of Chemistry
SN - 0008-4042
IS - 5
ER -