Abstract
A copper-catalyzed enantioselective Claisen rearrangement of easily accessible enolphosphonates using the commercially available PhBOX as the chiral ligand was developed. A wide range of rearrangement products with contiguous tertiary and all-carbon quaternary centers were obtained in excellent yields and stereoselectivities. The α-ketophosphonate substituent in the products could be easily transformed into other functional groups.
| Original language | English |
|---|---|
| Pages (from-to) | 8264-8267 |
| Number of pages | 4 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 51 |
| Issue number | 33 |
| DOIs | |
| Publication status | Published - 2012 Aug 13 |
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Keywords
- asymmetric catalysis
- BOX ligands
- Claisen rearrangement
- copper
- quaternary carbon centers
ASJC Scopus subject areas
- Chemistry(all)
- Catalysis
Cite this
Catalytic asymmetric claisen rearrangement of enolphosphonates : Construction of vicinal tertiary and all-carbon quaternary centers. / Tan, Jiajing; Cheon, Cheol-Hong; Yamamoto, Hisashi.
In: Angewandte Chemie - International Edition, Vol. 51, No. 33, 13.08.2012, p. 8264-8267.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Catalytic asymmetric claisen rearrangement of enolphosphonates
T2 - Construction of vicinal tertiary and all-carbon quaternary centers
AU - Tan, Jiajing
AU - Cheon, Cheol-Hong
AU - Yamamoto, Hisashi
PY - 2012/8/13
Y1 - 2012/8/13
N2 - A copper-catalyzed enantioselective Claisen rearrangement of easily accessible enolphosphonates using the commercially available PhBOX as the chiral ligand was developed. A wide range of rearrangement products with contiguous tertiary and all-carbon quaternary centers were obtained in excellent yields and stereoselectivities. The α-ketophosphonate substituent in the products could be easily transformed into other functional groups.
AB - A copper-catalyzed enantioselective Claisen rearrangement of easily accessible enolphosphonates using the commercially available PhBOX as the chiral ligand was developed. A wide range of rearrangement products with contiguous tertiary and all-carbon quaternary centers were obtained in excellent yields and stereoselectivities. The α-ketophosphonate substituent in the products could be easily transformed into other functional groups.
KW - asymmetric catalysis
KW - BOX ligands
KW - Claisen rearrangement
KW - copper
KW - quaternary carbon centers
UR - http://www.scopus.com/inward/record.url?scp=84864867846&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84864867846&partnerID=8YFLogxK
U2 - 10.1002/anie.201203092
DO - 10.1002/anie.201203092
M3 - Article
C2 - 22821885
AN - SCOPUS:84864867846
VL - 51
SP - 8264
EP - 8267
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 33
ER -