Abstract
The gold(I)-catalyzed intramolecular hydroamination of cyclohexa-1,3-dienes bearing an arylsulfonamide at the C-5 position proceeds in a 1,4-addition manner to afford hexahydroindole derivatives in a diastereoselective fashion and in good yields, whereas octahydrocyclohepta[b]pyrrole derivatives can be obtained from seven-membered ring substrates under the same reaction conditions. Coordination of the gold(I) species to the 1,3-diene at the double bond adjacent to the arylsulfonamide tether gave an η2-alkene gold complex. The anti-attack of the sulfonamide to the η2-alkene gold complex at the terminal position of the 1,3-diene resulted in the formation of the fused bicyclic ring with a newly formed Au-C bond at the allylic position. Allylic rearrangement of the η1-allylgold complex followed by protodemetalation provided the fused heterobicyclic skeletons and regenerated the catalyst.
| Original language | English |
|---|---|
| Pages (from-to) | 4789-4794 |
| Number of pages | 6 |
| Journal | Tetrahedron |
| Volume | 65 |
| Issue number | 25 |
| DOIs | |
| Publication status | Published - 2009 Jun 20 |
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Keywords
- Cycloheptadiene
- Cyclohexadiene
- Gold-catalyzed
- Hexahydroindoles
- Hydroamination
- Intramolecular
- Octahydrocyclohepta[b]pyrroles
- Sulfonamide
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
Cite this
Stereoselective synthesis of hexahydroindoles and octahydrocyclohepta[b]pyrroles via gold(I)-catalyzed intramolecular 1,4-hydroamination of cyclic 1,3-dienes. / Yeh, Ming-Chang P.; Pai, Hui Fen; Lin, Zao Jun; Lee, Bo Ren.
In: Tetrahedron, Vol. 65, No. 25, 20.06.2009, p. 4789-4794.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Stereoselective synthesis of hexahydroindoles and octahydrocyclohepta[b]pyrroles via gold(I)-catalyzed intramolecular 1,4-hydroamination of cyclic 1,3-dienes
AU - Yeh, Ming-Chang P.
AU - Pai, Hui Fen
AU - Lin, Zao Jun
AU - Lee, Bo Ren
PY - 2009/6/20
Y1 - 2009/6/20
N2 - The gold(I)-catalyzed intramolecular hydroamination of cyclohexa-1,3-dienes bearing an arylsulfonamide at the C-5 position proceeds in a 1,4-addition manner to afford hexahydroindole derivatives in a diastereoselective fashion and in good yields, whereas octahydrocyclohepta[b]pyrrole derivatives can be obtained from seven-membered ring substrates under the same reaction conditions. Coordination of the gold(I) species to the 1,3-diene at the double bond adjacent to the arylsulfonamide tether gave an η2-alkene gold complex. The anti-attack of the sulfonamide to the η2-alkene gold complex at the terminal position of the 1,3-diene resulted in the formation of the fused bicyclic ring with a newly formed Au-C bond at the allylic position. Allylic rearrangement of the η1-allylgold complex followed by protodemetalation provided the fused heterobicyclic skeletons and regenerated the catalyst.
AB - The gold(I)-catalyzed intramolecular hydroamination of cyclohexa-1,3-dienes bearing an arylsulfonamide at the C-5 position proceeds in a 1,4-addition manner to afford hexahydroindole derivatives in a diastereoselective fashion and in good yields, whereas octahydrocyclohepta[b]pyrrole derivatives can be obtained from seven-membered ring substrates under the same reaction conditions. Coordination of the gold(I) species to the 1,3-diene at the double bond adjacent to the arylsulfonamide tether gave an η2-alkene gold complex. The anti-attack of the sulfonamide to the η2-alkene gold complex at the terminal position of the 1,3-diene resulted in the formation of the fused bicyclic ring with a newly formed Au-C bond at the allylic position. Allylic rearrangement of the η1-allylgold complex followed by protodemetalation provided the fused heterobicyclic skeletons and regenerated the catalyst.
KW - Cycloheptadiene
KW - Cyclohexadiene
KW - Gold-catalyzed
KW - Hexahydroindoles
KW - Hydroamination
KW - Intramolecular
KW - Octahydrocyclohepta[b]pyrroles
KW - Sulfonamide
UR - http://www.scopus.com/inward/record.url?scp=65549099123&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=65549099123&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2009.04.064
DO - 10.1016/j.tet.2009.04.064
M3 - Article
AN - SCOPUS:65549099123
VL - 65
SP - 4789
EP - 4794
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 25
ER -