Abstract
It's do or diene: Stable chiral bicyclo[2.2.1]diene ligands were synthesized from (-)-5-oxobornyl acetate and utilized in the asymmetric 1,4-addition reaction of arylboronic acids with acyclic α,β- unsaturated compounds. Low catalytic loading of the complex, generated in situ from 1 and [{RhCl(C2H4)2}2], provides adducts in good to excellent yields and excellent enantioselectivities. This method was used for the formal total synthesis of (-)-indatraline.
| Original language | English |
|---|---|
| Pages (from-to) | 11405-11409 |
| Number of pages | 5 |
| Journal | Chemistry - A European Journal |
| Volume | 17 |
| Issue number | 41 |
| DOIs | |
| Publication status | Published - 2011 Oct 4 |
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Keywords
- addition reactions
- arylboronic acids
- asymmetric catalysis
- diene ligands
- enantioselectivity
- indatraline
- rhodium
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
Cite this
Highly enantioselective rhodium-catalyzed asymmetric 1,4-addition reactions of arylboronic acids to acyclic α,β-unsaturated compounds : The formal synthesis of (-)-indatraline. / Wei, Wei Ting; Yeh, Jiann Yih; Kuo, Ting Shen; Wu, Hsyueh-Liang.
In: Chemistry - A European Journal, Vol. 17, No. 41, 04.10.2011, p. 11405-11409.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Highly enantioselective rhodium-catalyzed asymmetric 1,4-addition reactions of arylboronic acids to acyclic α,β-unsaturated compounds
T2 - The formal synthesis of (-)-indatraline
AU - Wei, Wei Ting
AU - Yeh, Jiann Yih
AU - Kuo, Ting Shen
AU - Wu, Hsyueh-Liang
PY - 2011/10/4
Y1 - 2011/10/4
N2 - It's do or diene: Stable chiral bicyclo[2.2.1]diene ligands were synthesized from (-)-5-oxobornyl acetate and utilized in the asymmetric 1,4-addition reaction of arylboronic acids with acyclic α,β- unsaturated compounds. Low catalytic loading of the complex, generated in situ from 1 and [{RhCl(C2H4)2}2], provides adducts in good to excellent yields and excellent enantioselectivities. This method was used for the formal total synthesis of (-)-indatraline.
AB - It's do or diene: Stable chiral bicyclo[2.2.1]diene ligands were synthesized from (-)-5-oxobornyl acetate and utilized in the asymmetric 1,4-addition reaction of arylboronic acids with acyclic α,β- unsaturated compounds. Low catalytic loading of the complex, generated in situ from 1 and [{RhCl(C2H4)2}2], provides adducts in good to excellent yields and excellent enantioselectivities. This method was used for the formal total synthesis of (-)-indatraline.
KW - addition reactions
KW - arylboronic acids
KW - asymmetric catalysis
KW - diene ligands
KW - enantioselectivity
KW - indatraline
KW - rhodium
UR - http://www.scopus.com/inward/record.url?scp=80053211491&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=80053211491&partnerID=8YFLogxK
U2 - 10.1002/chem.201102073
DO - 10.1002/chem.201102073
M3 - Article
C2 - 21882278
AN - SCOPUS:80053211491
VL - 17
SP - 11405
EP - 11409
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 41
ER -