Abstract
Enantioselective synthesis of azepine-fused planar-chiral ferrocenes was achieved by the chiral cationic Pt-catalyzed intramolecular cycloisomerization of N-propargyl-2-ferrocenylanilines. A mechanistic study using an N-allenyl analogue indicated that the reaction proceeded selectively in a 7-exo-dig manner along with isomerization of the exo-olefin moiety. A methanesulfonylamino tether was crucial for selective cycloisomerization. This is the first example of the enantioselective synthesis of heteropin-fused planar-chiral ferrocenes.
| Original language | English |
|---|---|
| Journal | Organometallics |
| DOIs | |
| Publication status | Accepted/In press - 2019 Jan 1 |
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ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry
Cite this
Catalytic Enantioselective Synthesis of Azepine-Fused Planar-Chiral Ferrocenes by Pt-Catalyzed Cycloisomerization. / Ito, Mamoru; Okamura, Moeka; Kanyiva, Stephen Kyalo; Shibata, Takanori.
In: Organometallics, 01.01.2019.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Catalytic Enantioselective Synthesis of Azepine-Fused Planar-Chiral Ferrocenes by Pt-Catalyzed Cycloisomerization
AU - Ito, Mamoru
AU - Okamura, Moeka
AU - Kanyiva, Stephen Kyalo
AU - Shibata, Takanori
PY - 2019/1/1
Y1 - 2019/1/1
N2 - Enantioselective synthesis of azepine-fused planar-chiral ferrocenes was achieved by the chiral cationic Pt-catalyzed intramolecular cycloisomerization of N-propargyl-2-ferrocenylanilines. A mechanistic study using an N-allenyl analogue indicated that the reaction proceeded selectively in a 7-exo-dig manner along with isomerization of the exo-olefin moiety. A methanesulfonylamino tether was crucial for selective cycloisomerization. This is the first example of the enantioselective synthesis of heteropin-fused planar-chiral ferrocenes.
AB - Enantioselective synthesis of azepine-fused planar-chiral ferrocenes was achieved by the chiral cationic Pt-catalyzed intramolecular cycloisomerization of N-propargyl-2-ferrocenylanilines. A mechanistic study using an N-allenyl analogue indicated that the reaction proceeded selectively in a 7-exo-dig manner along with isomerization of the exo-olefin moiety. A methanesulfonylamino tether was crucial for selective cycloisomerization. This is the first example of the enantioselective synthesis of heteropin-fused planar-chiral ferrocenes.
UR - http://www.scopus.com/inward/record.url?scp=85071665733&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85071665733&partnerID=8YFLogxK
U2 - 10.1021/acs.organomet.9b00422
DO - 10.1021/acs.organomet.9b00422
M3 - Article
AN - SCOPUS:85071665733
JO - Organometallics
JF - Organometallics
SN - 0276-7333
ER -