Abstract
An enantioselective addition of arylboronic acids and α-ketoesters promoted by a Rhodium(I)-chiral diene catalyst is reported. The transformation proceeds regioselectively in the presence of as low as 0.5 mol% of the catalyst generated in situ from a Rhodium(I) salt and diene L1, which is a bicyclo[2.2.1] ligand scaffold bearing 2,5 dinaphthyl substituents, to afford tertiary chiral α-hydroxy esters with high stereoselectivities (90–99% ee's) and in 50–>99% yields. The method provides an expeditious and enantioselective synthesis of (S)-flutriafol. (Figure presented.).
| Original language | English |
|---|---|
| Pages (from-to) | 3381-3390 |
| Number of pages | 10 |
| Journal | Advanced Synthesis and Catalysis |
| Volume | 360 |
| Issue number | 17 |
| DOIs | |
| Publication status | Published - 2018 Sep 3 |
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Keywords
- arylation
- asymmetric catalysis
- rhodium
- tertiary α-hydroxy esters
- α-ketoesters
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
Cite this
Efficient and Enantioselective Rhodium(I)-Catalyzed Arylation of α-Ketoesters : Synthesis of (S)-Flutriafol. / Chang, Chiung An; Uang, Tsung Ying; Jian, Jia Hong; Zhou, Meng Yi; Chen, Ming Liang; Kuo, Ting Shen; Wu, Ping Yu; Wu, Hsyueh Liang.
In: Advanced Synthesis and Catalysis, Vol. 360, No. 17, 03.09.2018, p. 3381-3390.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Efficient and Enantioselective Rhodium(I)-Catalyzed Arylation of α-Ketoesters
T2 - Synthesis of (S)-Flutriafol
AU - Chang, Chiung An
AU - Uang, Tsung Ying
AU - Jian, Jia Hong
AU - Zhou, Meng Yi
AU - Chen, Ming Liang
AU - Kuo, Ting Shen
AU - Wu, Ping Yu
AU - Wu, Hsyueh Liang
PY - 2018/9/3
Y1 - 2018/9/3
N2 - An enantioselective addition of arylboronic acids and α-ketoesters promoted by a Rhodium(I)-chiral diene catalyst is reported. The transformation proceeds regioselectively in the presence of as low as 0.5 mol% of the catalyst generated in situ from a Rhodium(I) salt and diene L1, which is a bicyclo[2.2.1] ligand scaffold bearing 2,5 dinaphthyl substituents, to afford tertiary chiral α-hydroxy esters with high stereoselectivities (90–99% ee's) and in 50–>99% yields. The method provides an expeditious and enantioselective synthesis of (S)-flutriafol. (Figure presented.).
AB - An enantioselective addition of arylboronic acids and α-ketoesters promoted by a Rhodium(I)-chiral diene catalyst is reported. The transformation proceeds regioselectively in the presence of as low as 0.5 mol% of the catalyst generated in situ from a Rhodium(I) salt and diene L1, which is a bicyclo[2.2.1] ligand scaffold bearing 2,5 dinaphthyl substituents, to afford tertiary chiral α-hydroxy esters with high stereoselectivities (90–99% ee's) and in 50–>99% yields. The method provides an expeditious and enantioselective synthesis of (S)-flutriafol. (Figure presented.).
KW - arylation
KW - asymmetric catalysis
KW - rhodium
KW - tertiary α-hydroxy esters
KW - α-ketoesters
UR - http://www.scopus.com/inward/record.url?scp=85050871842&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85050871842&partnerID=8YFLogxK
U2 - 10.1002/adsc.201800575
DO - 10.1002/adsc.201800575
M3 - Article
VL - 360
SP - 3381
EP - 3390
JO - Advanced Synthesis and Catalysis
JF - Advanced Synthesis and Catalysis
SN - 1615-4150
IS - 17
ER -